4-(Hydroxymethyl)benzeneboronic acid → {3'-[4-Trifluoromethyl-6-(4-trifluoromethyl-phenyl)-pyrimidin-2-yl]-biphenyl-4-yl}-methanol

HRID 1928098Notes

Reaction equation

HRID 1928098 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:8]2[N:13]=[C:12]([C:14]([F:17])([F:16])[F:15])[CH:11]=[C:10]([C:18]3[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:20][CH:19]=3)[N:9]=2)[CH:5]=[CH:6][CH:7]=1.[OH:28][CH2:29][C:30]1[CH:35]=[CH:34][C:33](B(O)O)=[CH:32][CH:31]=1>>[F:15][C:14]([F:17])([F:16])[C:12]1[CH:11]=[C:10]([C:18]2[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:20][CH:19]=2)[N:9]=[C:8]([C:4]2[CH:3]=[C:2]([C:33]3[CH:34]=[CH:35][C:30]([CH2:29][OH:28])=[CH:31][CH:32]=3)[CH:7]=[CH:6][CH:5]=2)[N:13]=1

Participants

3

Reactant 2

HCID 27347064-(Hydroxymethyl)benzeneboronic acidHCID 574687272-(3-Bromo-phenyl)-4-trifluoromethyl-6-(4-trifluoromethylphenyl)-pyrimidine

Product 1

HCID 57468876{3'-[4-Trifluoromethyl-6-(4-trifluoromethyl-phenyl)-pyrimidin-2-yl]-biphenyl-4-yl}-methanol

Procedure

The title compound was prepared from 2-(3-bromo-phenyl)-4-trifluoromethyl-6-(4-trifluoromethyl-phenyl)-pyrimidine (example E.3) (0.22 g, 0.5 mmol) and commercially available 4-hydroxymethyl-phenyl-boronic acid (0.09 g, 0.6 mmol) according to the general procedure VI. Obtained as a white solid (0.199 g, 54%). MS (ISP) 475.1 [(M+H)+]; mp 171° C.

Sources & evidence

ORD record
ord-5cf6d38aaee6474fb4bb388a9f03fadf
Source dataset
uspto-grants-2012_05
Patent number
US08183262B2

Reaction notes

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