Water → 4-fluoro-2-hydroxy-N-[2-[2-[[3-(trifluoromethyl)phenyl]sulfonyl]-ethylsulfanyl]-pyridin-3-yl]benzamide

HRID 888266Notes

Reaction equation

[F:1][C:2]1[CH:32]=[CH:31][C:5]([C:6]([NH:8][C:9]2[C:10]([S:15][CH2:16][CH2:17][S:18]([C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:30])([F:29])[F:28])[CH:22]=3)(=[O:20])=[O:19])=[N:11][CH:12]=[CH:13][CH:14]=2)=[O:7])=[C:4]([O:33]C)[CH:3]=1.B(Br)(Br)Br.O.C([O-])(O)=O.[Na+]>C(Cl)Cl>[F:1][C:2]1[CH:32]=[CH:31][C:5]([C:6]([NH:8][C:9]2[C:10]([S:15][CH2:16][CH2:17][S:18]([C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:28])([F:29])[F:30])[CH:22]=3)(=[O:20])=[O:19])=[N:11][CH:12]=[CH:13][CH:14]=2)=[O:7])=[C:4]([OH:33])[CH:3]=1

Participants

Conditions

Temperature: -78 °C

Procedure

A solution of 515 mg (1.0 mmol) 4-fluoro-2-methoxy-N-[2-[2-[[3-(trifluoromethyl)phenyl]sulfonyl]-ethylsulfanyl]-pyridin-3-yl]benzamide (example compound 50) in DCM (5 ml) was cooled to −78° C. 5 ml (1 M in DCM, 5.0 mmol) BBr3 were added at this temperature and the mixture was stirred for 1 h at −78° C. Then the reaction solution was poured into an iced water mixture and it was adjusted to pH 8 with NaHCO3. Then it was extracted with DCM and the organic phase was washed with water and brine, dried over Na2SO4, filtered and concentrated to small volume under vacuum. 290 mg of 4-fluoro-2-hydroxy-N-[2-[2-[[3-(trifluoromethyl)phenyl]sulfonyl]-ethylsulfanyl]-pyridin-3-yl]benzamide were obtained as residue. MS: m/z 501.0 [M+H]+.

Workup

customwas cooled to −78° C
extractionThen it was extracted with DCM
washthe organic phase was washed with water and brine
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated to small volume under vacuum

Sources & evidence

ORD record: ord-d82d42c106534f1faefbb1408396d8a9
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08247573B2

Reaction notes

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