Potassium Carbonate → HCID 131732306, compound

HRID 1424859Notes

Reaction equation

F[C:2]1[CH:3]=[CH:4][C:5]([N+:10]([O-:12])=[O:11])=[C:6]([CH:9]=1)[C:7]#[N:8].[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[O:21][C:22]3[CH:32]=[C:31]([NH:33][S:34]([CH3:37])(=[O:36])=[O:35])[C:30]([CH:38]4[CH2:40][CH2:39]4)=[CH:29][C:23]=3[C:24]=2[C:25]([NH:27][CH3:28])=[O:26])=[CH:16][CH:15]=1.C([O-])([O-])=O.[K+].[K+]>COCCOC.O.CCOC(C)=O>[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[O:21][C:22]3[CH:32]=[C:31]([N:33]([C:2]4[CH:3]=[CH:4][C:5]([N+:10]([O-:12])=[O:11])=[C:6]([C:7]#[N:8])[CH:9]=4)[S:34]([CH3:37])(=[O:35])=[O:36])[C:30]([CH:38]4[CH2:40][CH2:39]4)=[CH:29][C:23]=3[C:24]=2[C:25]([NH:27][CH3:28])=[O:26])=[CH:16][CH:15]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 5-fluoro-2-nitrobenzonitrile (0.656 mL, 5.73 mmol), 2-(4-chlorophenyl)-5-cyclopropyl-N-methyl-6-(methylsulfonamido)benzofuran-3-carboxamide (2.0 g, 4.77 mmol) and K2CO3 (1.980 g, 14.32 mmol) in 1,2-dimethoxyethane (20 mL) and water (5.0 mL) in a seal tube was heated to 80° C. overnight. Cooled down to room temperature, it was diluted with EtOAc. The mixture was washed with water and brine, dried over Na2SO4. It was concentrated to dryness to give the crude product (>99%) as yellow solid which was used for the next step without further purification. LCMS (m/z, ES+)=565 (M+H+).

Workup

temperatureCooled down to room temperature
washThe mixture was washed with water and brine
dry with materialdried over Na2SO4
concentrationIt was concentrated to dryness

Sources & evidence

ORD record: ord-968b20cab99144f4be6d928e4d826af1
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08927593B2

Reaction notes

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