Cesium carbonate → HCID 58007531, compound

HRID 1094416Notes

Reaction equation

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

Participants

Conditions

Temperature: 120 °C

Procedure

To 2-(6-trifluoromethyl-pyridin-3-yl)-ethylamine (955 mg, 5.0 mmol) were added 6-bromo-2,3-dihydro-benzofuran (1.00 g, 5.0 mmol), cuprous iodide (48 mg, 0.25 mmol) and cesium carbonate (3.27 g, 10.0 mmol) under an Ar-atmosphere. Then DMF (2.0 ml) and 2-acetylcyclohexanone (133 μl, 0.10 mmol) were added and the reaction mixture was stirred for 2 h at 120° C. It was cooled to ambient temperature and separated between TBME (40 ml) and water (15 ml). The organic layer was 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 (803 mg, 52%) as a yellow oil. MS m/e: 309.3 [M+H]+.

Workup

temperatureIt was cooled to ambient temperature
customseparated between TBME (40 ml) and water (15 ml)
washThe organic layer was 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-5c8afb975ff1426d835a9b535a06bf3d
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08133909B2

Reaction notes

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