(3,5-Difluorophenyl)boronic acid → 2-(3,5-Difluoro-4''-chloro-3''-trifluoromethyl-[1,1';3',1'']terphenyl-5'-yl)-4-methyl-pentanoic acid methyl ester

HRID 426350Notes

Reaction equation

HRID 426350 reaction equation
[CH3:1][O:2][C:3](=[O:34])[CH:4]([C:9]1[CH:10]=[C:11]([C:23]2[CH:28]=[CH:27][C:26]([Cl:29])=[C:25]([C:30]([F:33])([F:32])[F:31])[CH:24]=2)[CH:12]=[C:13](OS(C(F)(F)F)(=O)=O)[CH:14]=1)[CH2:5][CH:6]([CH3:8])[CH3:7].[F:35][C:36]1[CH:37]=[C:38](B(O)O)[CH:39]=[C:40]([F:42])[CH:41]=1>>[CH3:1][O:2][C:3](=[O:34])[CH:4]([C:9]1[CH:10]=[C:11]([C:23]2[CH:28]=[CH:27][C:26]([Cl:29])=[C:25]([C:30]([F:33])([F:32])[F:31])[CH:24]=2)[CH:12]=[C:13]([C:38]2[CH:37]=[C:36]([F:35])[CH:41]=[C:40]([F:42])[CH:39]=2)[CH:14]=1)[CH2:5][CH:6]([CH3:8])[CH3:7]

Participants

3

Reactant 2

HCID 2734338(3,5-Difluorophenyl)boronic acidHCID 577549642-(4'-Chloro-5-trifluoromethanesulfonyloxy-3'-trifluoromethyl-biphenyl-3-yl)-4-methyl-pentanoic acid methyl ester2×

Product 1

HCID 590047362-(3,5-Difluoro-4''-chloro-3''-trifluoromethyl-[1,1';3',1'']terphenyl-5'-yl)-4-methyl-pentanoic acid methyl esterYield 40%

Procedure

The title compound was prepared in 40% yield from 2-(4′-chloro-5-trifluoromethanesulfonyloxy-3′-trifluoromethyl-biphenyl-3-yl)-4-methyl-pentanoic acid methyl ester (prepared in Intermediate C) and 3,5-difluorophenylboronic acid under the conditions described in Example 26, step (d). 1H-NMR (400 MHz, CDCl3): δ 7.90 (s, 1H), 7.72 (d, 1H), 7.60 (d, 1H), 7.58 (s, 1H), 7.52 (s, 2H), 7.15 (d, 2H), 6.83 (t, 1H), 3.80 (t, 1H), 3.70 (s, 3H), 2.04 (m, 1H), 1.73 (m, 1H), 0.95 (d, 6H.

Sources & evidence

ORD record
ord-ae1a8cb076fc4ce48af2043a2149a18e
Source dataset
uspto-grants-2012_01
Patent number
US08106236B2

Reaction notes

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