Water → N-(2-Fluoro-4-nitrophenyl)-N-methyl-2-(1-methyl-1H-imidazol-4-yl)thieno[3,2-b]pyridin-7-amine

HRID 2193773Notes

Reaction equation

[CH3:1][NH:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]2[CH:9]=[C:10]([C:12]3[N:13]=[CH:14][N:15]([CH3:17])[CH:16]=3)[S:11][C:4]=12.[F:18][C:19]1[CH:20]=[C:21]([N+:26]([O-:28])=[O:27])[CH:22]=[CH:23][C:24]=1F.C(=O)([O-])[O-].[Cs+].[Cs+].O>CN(C=O)C>[F:18][C:19]1[CH:20]=[C:21]([N+:26]([O-:28])=[O:27])[CH:22]=[CH:23][C:24]=1[N:2]([CH3:1])[C:3]1[CH:8]=[CH:7][N:6]=[C:5]2[CH:9]=[C:10]([C:12]3[N:13]=[CH:14][N:15]([CH3:17])[CH:16]=3)[S:11][C:4]=12

Participants

Conditions

Temperature: 85 °C

Procedure

A stirred suspension of 344 (500 mg, ˜2 mmol), 3,4-difluoronitrobenzene (795 mg, 5 mmol) and cesium carbonate (1.63 g, 5 mmol) in anhydrous DMF (50 ml) was heated at 85° C. under nitrogen for 7 h. The temperature was allowed to cool down to room temperature. The reaction mixture was poured into water, and extracted with dichloromethane. The combined organic phase was concentrated and directly purified twice by flash column chromatography (eluents 2% of NH4OH in methanol/CH2Cl2: 5/95 to 10/90) to afford title compound 345 (144 mg, 19% yield) as a sticky yellow solid. MS (m/z): 384.0 (M+H)+.

Workup

temperatureto cool down to room temperature
extractionextracted with dichloromethane
concentrationThe combined organic phase was concentrated
customdirectly purified twice by flash column chromatography (eluents 2% of NH4OH in methanol/CH2Cl2: 5/95 to 10/90)

Sources & evidence

ORD record: ord-9d27b56ae40642dd8b3a711621e9bc45
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08329726B2

Reaction notes

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