Potassium Carbonate → HCID 59739596, compound

HRID 1192965Notes

Reaction equation

C[S:2]([C:5]1[CH2:9][C:8]([CH3:11])([CH3:10])[O:7][N:6]=1)(=O)=O.O.[SH-].[Na+].O.O.CS(OO)(=O)=O.[Na].C(=O)([O-])[O-].[K+].[K+].Br[CH:31]([C:36]1[C:41]([F:42])=[CH:40][CH:39]=[CH:38][C:37]=1[F:43])[C:32]([F:35])([F:34])[F:33]>CN(C=O)C>[F:43][C:37]1[CH:38]=[CH:39][CH:40]=[C:41]([F:42])[C:36]=1[CH:31]([S:2][C:5]1[CH2:9][C:8]([CH3:11])([CH3:10])[O:7][N:6]=1)[C:32]([F:35])([F:34])[F:33]

Participants

Conditions

Temperature: 0 °C

Procedure

3-Methanesulfonyl-5,5-dimethyl-4,5-dihydroisoxazole (87 mg, 0.49 mmol), sodium hydrosulfide hydrate (73 mg, 0.99 mmol), sodium hydroxy methanesulfonate dihydrate (151 mg, 0.99 mmol) and potassium carbonate (136 mg, 0.99 mmol) were added to DMF (10 ml) at 0° C. and the mixture was stirred at 0° C. for 2 hours. 2-(1-Bromo-2,2,2-trifluoroethyl)-1,3-difluorobenzene (135 mg, 0.49 mmol) was added and the suspension was stirred at room temperature for 5 hours. The reaction was partitioned between water and ethyl acetate. The organic phase was washed with water, dried over magnesium sulfate and concentrated. The crude product was purified by chromatography on silica gel (eluent: ethyl acetate/hexane) to give the product as a white solid (55 mg, 35% yield). 1H-NMR (400 MHz, CDCl3): 1.41 (3H, s, Me), 1.45 (3H, s, Me), 2.80 (1H, d, CH2), 2.82 (1H, d, CH2), 5.98 (1H, m, CH), 6.97 (2H, m, CH), 7.37 (1H, m, CH).

Workup

stirringthe suspension was stirred at room temperature for 5 hours
customThe reaction was partitioned between water and ethyl acetate
washThe organic phase was washed with water
dry with materialdried over magnesium sulfate
concentrationconcentrated
customThe crude product was purified by chromatography on silica gel (eluent: ethyl acetate/hexane)

Sources & evidence

ORD record: ord-23dec8a10ea74e4bb33ce20450709bf3
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08680290B2

Reaction notes

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