3,4-Difluorobenzeneboronic acid → [1,1'-Biphenyl]-4-sulfonamide, 3',4'-difluoro-N-(5-hydroxypentyl)-

HRID 2425140Notes

Reaction equation

HRID 2425140 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][NH:7][S:8]([C:11]1[CH:16]=[CH:15][C:14](Br)=[CH:13][CH:12]=1)(=[O:10])=[O:9].[F:18][C:19]1[CH:20]=[C:21](B(O)O)[CH:22]=[CH:23][C:24]=1[F:25]>>[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][NH:7][S:8]([C:11]1[CH:16]=[CH:15][C:14]([C:22]2[CH:21]=[CH:20][C:19]([F:18])=[C:24]([F:25])[CH:23]=2)=[CH:13][CH:12]=1)(=[O:10])=[O:9]

Participants

3

Reactant 2

HCID 27343373,4-Difluorobenzeneboronic acidHCID 160947214-Bromo-N-(5-hydroxypentyl)benzene-1-sulfonamide

Product 1

HCID 11703139[1,1'-Biphenyl]-4-sulfonamide, 3',4'-difluoro-N-(5-hydroxypentyl)-

Procedure

Using a method analogous to that described in Example 40, 4-bromophenyl-sulfonic acid-(5-hydroxypentyl)-amide and 3,4-difluorophenyl boronic acid were reacted to give the title compound as a white solid. δC (CDCl3, 62.9 MHz): 22.7, 29.3, 31.9, 43.1, 62.5, 116.4 (d, J 17.6), 118.0 (d, J 17.6), 123.5 (d, J 4.9), 127.6, 127.8, 136.4 (m), 139.2, 143.3, 150.5 (d, J 250.0) and 150.7 (d, J 250.0).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-0c5e287d177043b5a617a9640eff140f
Source dataset
uspto-grants-2011_06
Patent number
US07964643B2

Reaction notes

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