Khoom npe	N-(6-Bromoimidazo[1,2-a]pyridin-2-yl)-2,2,2-trifluoroacetamide
CAS Nr	504413-35-8
Molecular Formula	C₉H₅BrF₃N₃O
Molecular Luj	308.06
SMILES Code	O=C(NC1=CN2C=C(Br)C=CC2=N1)C(F)(F)F
MDL Nr.	TIAB SA 11976190
Pub Chem ID	12065953
InChI Key	BUYPVRDWQVLXDL-UHFFFAOYSA-N

Synthesis Txoj Kev

Synthesis: 504413-35-8

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1005785-49-8		407-25-0		504413-35-8

Productivity	Synthesis tej yam kev mob	Cov txheej txheem sim
96%	Kub ntawm 60 degree; rau 2h;.	Kauj Ruam 3. N-(6-Bromoimidazo[1,2-a]pyridin-2-yl)-2,2,2-trifluoroacetamide Rau 250-mL puag ncig-hauv qab lub khob ntim nrog lub reflux condenser ntxiv 2-(5-bromo-2-(4-methylphenylsulfonamido)pyridin-1(2H)-yl)acetamide (10.0 g, 26.0 mmol), 1,2-dichloroethane (150 mL), thiab thaum kawg trifluoroacetic anhydride (18.4 mL, 130 mmol). Qhov sib tov yog nplawm ntawm 60℃rau 2 teev. Cov tshuaj tau txias rau chav tsev kub thiab concentrated. Cov khoom tiav tau yaj hauv DCM (300 mL) thiab ntxuav nrog 10% NaHCO₃ (2 × 100 mL). Lub aqueous ntxuav tau muab rho tawm nrog DCM (2 × 100 mL) thiab ua ke nrog thawj DCM tov. Cov kev daws teeb meem ua ke tau ntxuav nrog brine (100 mL), qhuav (Na2SO4) thiab muaj zog kom muab cov ntsiab lus sib xyaw ua cov khoom siv tawv tawv uas tau siv yam tsis muaj kev lim dej ntxiv (7.72 g, 96%).
52%	Theem #1: Reflux Theem #2: Nrog sodium hydrogencarbonate Hauv dej rau 0.25 h;	Trifluoroacetic anhydride (24 mL) tau maj mam ntxiv rau qhov sib xyaw ua ke ntawm 2-[(2Z)-5-bromo-2-{[(4-methylphenyl)sulfonyl]imino}pyridin-1(2H)-yl]acetamide (10.8mmol) (10. mL). Tom qab reflux rau 3 teev, cov tshuaj tiv thaiv sib tov yog concentrated nyob rau hauv lub siab txo, thiab lub resulting daj khoom raug tshem tawm nyob rau hauv saturated aqueous sodium bicarbonate tov, stirred rau 15 feeb, thiab lim. Cov khoom lag luam nyoos tau ua kom huv los ntawm silica gel flash chromatography (PE: EtOAc, 90:10) kom them taus lub npe compound raws li lub teeb daj (2.0 g, 52%). HPLC, Rt: 3.4 min (purity: 97%). UPLC/MS, M+ (ESI): 308.1, 310.1, M- (ESI): 306.1, 308.1. 1 H-NMR (DMSO-d6, 400MHz) δ 12.53 (brs, 1H), 8.94 (m, 1H), 8.1H, 7 (s, 8.1H), 7.39 (m., 1 H).

Chemical Properties

N-(6-Bromoimidazo[1,2-a]pyridin-2-yl)-2,2,2-trifluoroacetamide zoo nkaus li dawb mus rau dawb crystalline hmoov.Nws kwv yees qhov ceev yog 1.87±0.1 g / cm6.5, thiab qhov ruaj khov. Thaum muab ntim rau hauv qhov chaw qhuav ntawm chav tsev kub.Lub melting point yog nyob nruab nrab ntawm 154 thiab 158℃.Nws muaj cov dej solubility tsawg tab sis dissolves yooj yim hauv methanol, ethanol, THF, thiab DMF, nrog rau cov solubility nyob rau hauv ethyl acetate.Cov compound muaj ib qho electron-deficient imidazopyridine core, a bromine abonide substitus. nruab nrab tej yam kev mob tab sis muaj peev xwm hydrolyze nyob rau hauv lub sij hawm raug rau cov muaj zog acids los yog bases.Lub bromine yog nruab nrab reactive nyob rau hauv cross-coupling tshua.

Kev piav qhia

N-(6-Bromoimidazo[1,2-a]pyridin-2-yl)-2,2,2-trifluoroacetamide(CAS No.504413-35-8) yog ib tug functionalized imidazo[1,2-a]pyridine, ib tug privileged scaffold nyob rau hauv lub medicinal qauv. 6-txoj hauj lwm rau kev ua haujlwm ntxiv thiab muaj zog electron rho tawm pawg trifluoroacetamide ntawm imidazole nitrogen, uas hloov cov electron ceev ntawm lub nplhaib fused.

Siv

1.Electron-Deficient Building Block rau TADF Emitters
Cov hluav taws xob muaj zog- rho tawm pawg trifluoroacetamide ua rau cov khoom sib xyaw no yog ib qho kev lees paub zoo tshaj plaws.Nws yog ua ke nrog cov koom haum pub dawb xws li carbazole lossis acridine ntawm Buchwald -Hartwig amination ntawm qhov chaw bromine los tsim cov neeg pub dawb- txais cov molecules uas nthuav tawm thermal fluorescenced ncua sijhawm (TA) muaj txiaj ntsig, qis- tus nqi OLED emitters.

2.Covalent Probe rau Kinase Profiling
Lub bromine yog hloov nrog lub davhlau ya nyob twg alkyne ntawm Sonogashira coupling, tsim ib "clickable" sojntsuam.Qhov kev sojntsuam no, bearing lub imidazopyridine pharmacophore, yog siv nyob rau hauv kev sib tw kev ua si -raws li protein profiling (ABPP) los txheeb xyuas thiab validate tshiab ATP-binding sites.

3.Monomer rau Conjugated Microporous Polymers (CMPs)
Polymerized los ntawm Yamamoto los yog Sonogashira coupling cov tshuaj tiv thaiv siv bromine site.Qhov ua rau CMPs muaj thaj chaw siab, porosity mus tas li, thiab cov tshuaj lom neeg ruaj khov zoo heev, ua rau lawv muaj txiaj ntsig zoo heterogeneous photocatalysts rau cov organic transformations zoo li aerobic oxidations thiab cov pa phem degradation nyob rau hauv lub teeb pom kev.

4.Intermediate rau Antiviral Nucleoside Analogs
Cov bromine tau dhau los ntawm Pd-catalyzed cyanation, thiab cov txiaj ntsig nitrile raug txo thiab cyclized los ua ib qho tshiab triazole-fused nucleobase analog.Cov analogue no yog glycosylated los tsim muaj peev xwm nucleoside thim rov qab transcriptase inhibitors nrog kev ua haujlwm tawm tsam tshuaj - tiv thaiv kab mob HIV.

Cim npe nrov: n-(6-bromoimidazo[1,2-a]pyridin-2-yl)-2,2,2-trifluoroacetamide, Tuam Tshoj n-(6-bromoimidazo[1,2-a]pyridin-2-yl)-2,2,2-trifluoroacetamide manufacturers, lwm tus neeg