3-(Neopentyloxysulfonyl)phenylboronic acid → 3-{4-[4-Trifluoromethyl-6-(4-trifluoromethyl-phenyl)-pyrimidin-2-yl]-pyridin-2-yl}-benzenesulfonic acid 2,2-dimethyl-propyl ester

HRID 1989263Notes

Reaction equation

HRID 1989263 reaction equation
Cl[C:2]1[CH:7]=[C:6]([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:4][N:3]=1.[CH3:28][C:29]([CH3:45])([CH3:44])[CH2:30][O:31][S:32]([C:35]1[CH:36]=[C:37](B(O)O)[CH:38]=[CH:39][CH:40]=1)(=[O:34])=[O:33]>>[CH3:28][C:29]([CH3:45])([CH3:44])[CH2:30][O:31][S:32]([C:35]1[CH:36]=[CH:37][CH:38]=[C:39]([C:2]2[CH:7]=[C:6]([C:8]3[N:13]=[C:12]([C:14]([F:17])([F:16])[F:15])[CH:11]=[C:10]([C:18]4[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:20][CH:19]=4)[N:9]=3)[CH:5]=[CH:4][N:3]=2)[CH:40]=1)(=[O:34])=[O:33]

Participants

3

Reactant 2

HCID 467389673-(Neopentyloxysulfonyl)phenylboronic acidHCID 574687302-(2-Chloro-pyridin-4-yl)-4-trifluoromethyl-6-(4-trifluoromethyl-phenyl)-pyrimidine

Product 1

HCID 574688403-{4-[4-Trifluoromethyl-6-(4-trifluoromethyl-phenyl)-pyrimidin-2-yl]-pyridin-2-yl}-benzenesulfonic acid 2,2-dimethyl-propyl ester

Procedure

3-{4-[4-Trifluoromethyl-6-(4-trifluoromethyl-phenyl)-pyrimidin-2-yl]-pyridin-2-yl}-benzenesulfonic acid 2,2-dimethyl-propyl ester was prepared from 2-(2-chloro-pyridin-4-yl)-4-trifluoromethyl-6-(4-trifluoromethyl-phenyl)-pyrimidine (example E.6) (1.0 g, 2.5 mmol) and 3-(2,2-dimethyl-propyloxysulfonyl)-benzeneboronic acid (example F.4) (1.09 g, 4.0 mmol) according to the general procedure VI. Obtained as an off-white solid (1.28 g, 86%). MS (ISP) 595.7 [(M+H)+]; mp 168.5° C.

Sources & evidence

ORD record
ord-a6335cb4d02243ae9d301c75d5b57efb
Source dataset
uspto-grants-2010_01
Patent number
US07642264B2

Reaction notes

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