Cesium carbonate → HCID 58007491, compound

HRID 1094403Notes

Reaction equation

[F:1][C:2]([F:13])([F:12])[C:3]1[CH:4]=[CH:5][C:6]([CH2:9][CH2:10][NH2:11])=[N:7][CH:8]=1.Br[C:15]1[CH:23]=[C:22]2[C:18]([CH:19]=[CH:20][N:21]2[CH3:24])=[CH:17][CH:16]=1.C(=O)([O-])[O-].[Cs+].[Cs+].C(C1CCCCC1=O)(=O)C>CN(C=O)C>[CH3:24][N:21]1[C:22]2[C:18](=[CH:17][CH:16]=[C:15]([NH:11][CH2:10][CH2:9][C:6]3[CH:5]=[CH:4][C:3]([C:2]([F:12])([F:1])[F:13])=[CH:8][N:7]=3)[CH:23]=2)[CH:19]=[CH:20]1

Participants

Conditions

Temperature: 120 °C

Procedure

To 2-(5-trifluoromethyl-pyridin-2-yl)-ethylamine (200 mg, 1.05 mmol) was added 6-bromo-1-methyl-1H-indole (685 mg, 2.10 mmol), cuprous iodide (10 mg, 0.05 mmol) and cesium carbonate (685 mg, 2.1 mmol) under an argon atmosphere. Then DMF (400 μl) and 2-acetylcyclohexanone (28 μl, 0.21 mmol) were added and the reaction mixture was stirred for 4 h at 120° C. After cooling to ambient temperature the reaction mixture was separated between tert-butylmethylether (2×20 ml) and water (15 ml). The combined organic layers were washed with brine (15 ml) and dried over sodium sulfate. Concentration and purification by chromatography (SiO2, heptane:ethyl acetate=100:0 to 67:33) afforded the title compound (114 mg, 34%) as a light brown oil. MS m/e: 320.1 [M+H]+.

Workup

temperatureAfter cooling to ambient temperature the reaction mixture
customwas separated between tert-butylmethylether (2×20 ml) and water (15 ml)
washThe combined organic layers were washed with brine (15 ml)
dry with materialdried over sodium sulfate
concentrationConcentration and purification by chromatography (SiO2, heptane:ethyl acetate=100:0 to 67:33)

Sources & evidence

ORD record: ord-a1c5a4a7b3c540cab1df63891eb69458
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08133909B2

Reaction notes

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