HCID 22042580, compound → HCID 22042577, compound

HRID 2053665Notes

Reaction equation

[CH3:1][N:2]([C:12]1[CH:17]=[CH:16][C:15]([C:18](=[O:23])[C:19]([F:22])([F:21])[F:20])=[CH:14][CH:13]=1)[S:3]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)(=[O:5])=[O:4].[Cl:24][C:25]1[CH:30]=[CH:29][C:28]([Mg]Br)=[CH:27][CH:26]=1>C1COCC1>[Cl:24][C:25]1[CH:30]=[CH:29][C:28]([C:18]([C:15]2[CH:16]=[CH:17][C:12]([N:2]([CH3:1])[S:3]([C:6]3[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=3)(=[O:5])=[O:4])=[CH:13][CH:14]=2)([OH:23])[C:19]([F:21])([F:22])[F:20])=[CH:27][CH:26]=1

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of 0.2 g of N-methyl-N-(4-trifluoroacetyl-phenyl)-benzenesulfonamide in 10 mL of THF were added 0.7 mL of a 1 M solution 4-chlorophenyl magnesium bromide at −78° C. The resulting mixture was stirred at −78° C. for 4 hr. After this time, the reaction mixture was quenched by the addition of a saturated aqueous solution of ammonium chloride and extracted with EtOAc. The combined organic layers were washed with brine, dried over MgSO4, filtered and the filtrate was concentrated. The residue was purified by chromatography on silica gel (hexanes:EtOAc, 7:1) to give the title compound. 1H-NMR (CDCl3) δ 2.96 (br s, 1 H), 3.17 (s, 3 H), 7.10-7.59 (m, 13 H). Mass Spectrum (CI+) m/e=456 (M+1).

Workup

customAfter this time, the reaction mixture was quenched by the addition of a saturated aqueous solution of ammonium chloride
extractionextracted with EtOAc
washThe combined organic layers were washed with brine
dry with materialdried over MgSO4
filtrationfiltered
concentrationthe filtrate was concentrated
customThe residue was purified by chromatography on silica gel (hexanes:EtOAc, 7:1)

Sources & evidence

ORD record: ord-5574d0d0b565456cacb7ec6f40b445f6
Source dataset: uspto-grants-2008_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07326812B2

Reaction notes

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