Potassium Carbonate → HCID 131732306, compound

HRID 2272355Notes

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-2ffddc8491ae42b7928bb30f15a810ba
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09119868B2

Reaction notes

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