2,4-Difluorophenylboronic acid → [1,1'-Biphenyl]-4-sulfonamide, 2',4'-difluoro-N-(5-hydroxypentyl)-

HRID 2425138Notes

Reaction equation

HRID 2425138 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:24]=[C:23]([F:25])[CH:22]=[CH:21][C:20]=1B(O)O>>[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])=[CH:24][C:23]=2[F:25])=[CH:13][CH:12]=1)(=[O:10])=[O:9]

Participants

3

Reactant 2

HCID 27343342,4-Difluorophenylboronic acidHCID 160947214-Bromo-N-(5-hydroxypentyl)benzene-1-sulfonamide

Product 1

HCID 11631752[1,1'-Biphenyl]-4-sulfonamide, 2',4'-difluoro-N-(5-hydroxypentyl)-

Procedure

Using a method analogous to that described in Example 40, 4-bromophenyl-sulfonic acid-(5-hydroxypentyl)-amide and 2,4-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, 104.7 (t, J 25.8), 112.0 (dd, J 22.9 and 3.5), 127.3, 129.6, 131.5 (d, J 8.8), 131.5 (d, J 9.8), 139.1, 139.4, 159.8 (dd, J 252.0, 11.7) and 163.0 (dd, J 252.0, 11.7).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-7f2d32b0d7c642e1bd439d5e7742440e
Source dataset
uspto-grants-2011_06
Patent number
US07964643B2

Reaction notes

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