Cesium carbonate → HCID 58408282, compound

HRID 2192286Notes

Reaction equation

I[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][N:3]=1.OB(O)[C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][CH:20]=1)[N:17]([S:21]([C:24]1[CH:31]=[CH:30][C:27]([C:28]#[N:29])=[CH:26][CH:25]=1)(=[O:23])=[O:22])[CH2:16][CH2:15]2.C(=O)([O-])[O-].[Cs+].[Cs+]>O.CN(C)C=O.C(OCC)(=O)C>[CH3:9][O:8][C:5]1[CH:6]=[CH:7][C:2]([C:12]2[CH:13]=[C:14]3[C:18](=[CH:19][CH:20]=2)[N:17]([S:21]([C:24]2[CH:31]=[CH:30][C:27]([C:28]#[N:29])=[CH:26][CH:25]=2)(=[O:23])=[O:22])[CH2:16][CH2:15]3)=[N:3][CH:4]=1

Participants

Conditions

Temperature: 90 °C

Procedure

394 mg 2-Iodo-5-methoxypyridine, 500 mg 4-(5-Dihydroxyboranyl-2,3-dihydro-indole-1-sulfonyl)-benzonitrile and 1.49 g cesium carbonate were dissolved in a mixture of 5 ml water and 17 ml dimethylformamide. The reaction mixture was degassed with argon and then 88 mg tetrakis(triphenylphosphine)palladium(0) were added and the mixture heated to 90° C. for two hours. The cooled reaction mixture was diluted with 100 ml ethyl acetate and washed with 50 ml water and brine. The organic layer was dried over MgSO4 and the solvent removed in vacuo. The resulting crude material was purified by purified by chromatography on silica gel to obtain 307 mg 4-[5-(5-Methoxy-pyridin-2-yl)-2,3-dihydro-indole-1-sulfonyl]-benzonitrile.

Workup

customThe reaction mixture was degassed with argon
addition88 mg tetrakis(triphenylphosphine)palladium(0) were added
customThe cooled reaction mixture
washwashed with 50 ml water and brine
dry with materialThe organic layer was dried over MgSO4
customthe solvent removed in vacuo
customThe resulting crude material was purified
customby purified by chromatography on silica gel

Sources & evidence

ORD record: ord-5e6192e335144986a7a674496e6a4341
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08329725B2

Reaction notes

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