Cesium carbonate → 5-(6-Trifluoromethyl-pyridin-3-yl)-2,3-dihydro-1H-indole

HRID 2192288Notes

Reaction equation

[F:1][C:2]([F:13])([F:12])[C:3]1[CH:8]=[CH:7][C:6](B(O)O)=[CH:5][N:4]=1.Br[C:15]1[CH:16]=[C:17]2[C:21](=[CH:22][CH:23]=1)[NH:20][CH2:19][CH2:18]2.C(=O)([O-])[O-].[Cs+].[Cs+]>O.CN(C)C=O.C(OCC)(=O)C>[F:1][C:2]([F:13])([F:12])[C:3]1[N:4]=[CH:5][C:6]([C:15]2[CH:16]=[C:17]3[C:21](=[CH:22][CH:23]=2)[NH:20][CH2:19][CH2:18]3)=[CH:7][CH:8]=1

Participants

Conditions

Temperature: 100 °C

Procedure

1.6 g 2-(Trifluormethyl)pyridin-5-ylboronic acid, 1.66 g commercially available 5-Bromo-2,3-dihydro-1H-indole and 8.19 g cesium carbonate were dissolved in a mixture of 7 ml water and 21 ml dimethylformamide. The reaction mixture was degassed with argon and then 484 mg tetrakis(triphenylphosphine)palladium(0) were added and the mixture heated to 100° C. for two hours. The cooled reaction mixture was diluted with 200 ml ethyl acetate and washed with 100 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 885 mg 5-(6-Trifluoromethyl-pyridin-3-yl)-2,3-dihydro-1H-indole.

Workup

customThe reaction mixture was degassed with argon
addition484 mg tetrakis(triphenylphosphine)palladium(0) were added
customThe cooled reaction mixture
washwashed with 100 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-cba1fbfedf524d85bb931a9d3a1205f7
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08329725B2

Reaction notes

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