Water → ethyl 3-(4-cyano-3-fluorophenyl)-3H-imidazo[4,5-b]pyridine-2-carboxylate

HRID 2272710Notes

Reaction equation

[NH2:1][C:2]1[C:3]([NH:8][C:9]2[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[C:11]([F:17])[CH:10]=2)=[N:4][CH:5]=[CH:6][CH:7]=1.C(N(CC)CC)C.Cl[C:26](=O)[C:27]([O:29][CH2:30][CH3:31])=[O:28].O>ClCCl>[C:13]([C:12]1[CH:15]=[CH:16][C:9]([N:8]2[C:3]3=[N:4][CH:5]=[CH:6][CH:7]=[C:2]3[N:1]=[C:26]2[C:27]([O:29][CH2:30][CH3:31])=[O:28])=[CH:10][C:11]=1[F:17])#[N:14]

Participants

Conditions

Temperature: 0 °C

Procedure

To a 0° C. solution of 4-[(3-aminopyridin-2-yl)amino]-2-fluorobenzonitrile (C15) (300 mg, 1.31 mmol) and triethylamine (270 mg, 2.67 mmol) in dichloromethane (20 mL) was added ethyl chloro(oxo)acetate (220 mg, 1.61 mmol), and the solution was stirred at 0° C. for 2 hours. After addition of water (20 mL), the mixture was extracted with dichloromethane (3×20 mL); the combined organic layers were washed with saturated aqueous sodium chloride solution (20 mL), dried over sodium sulfate, filtered, concentrated under reduced pressure and purified by preparative thin layer chromatography on silica gel (Eluent: 10:1 dichloromethane/methanol) to afford the product as a yellow solid. Yield: 40 mg, 0.13 mmol, 10%. 1H NMR (400 MHz, CDCl3), characteristic peaks: δ 8.55 (d, J=5 Hz, 1H), 4.46 (q, J=7 Hz, 2H), 1.43 (t, J=7 Hz, 3H).

Workup

extractionthe mixture was extracted with dichloromethane (3×20 mL)
washthe combined organic layers were washed with saturated aqueous sodium chloride solution (20 mL)
dry with materialdried over sodium sulfate
filtrationfiltered
concentrationconcentrated under reduced pressure
custompurified by preparative thin layer chromatography on silica gel (Eluent: 10:1 dichloromethane/methanol)

Sources & evidence

ORD record: ord-0cbe7ebef7b24435a2362d5264be8d05
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09120788B2

Reaction notes

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