3-(tert-Butylaminosulphonyl)benzeneboronic acid → 3'-[4-(4-Chloro-phenyl)-6-methyl-pyrimidin-2-yl]-biphenyl-3-sulfonic acid tert-butylamide

HRID 1928150Notes

Reaction equation

HRID 1928150 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:8]2[N:13]=[C:12]([C:14]3[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=3)[CH:11]=[C:10]([CH3:21])[N:9]=2)[CH:5]=[CH:6][CH:7]=1.[C:22]([NH:26][S:27]([C:30]1[CH:31]=[C:32](B(O)O)[CH:33]=[CH:34][CH:35]=1)(=[O:29])=[O:28])([CH3:25])([CH3:24])[CH3:23]>>[C:22]([NH:26][S:27]([C:30]1[CH:35]=[C:34]([C:2]2[CH:7]=[CH:6][CH:5]=[C:4]([C:8]3[N:13]=[C:12]([C:14]4[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=4)[CH:11]=[C:10]([CH3:21])[N:9]=3)[CH:3]=2)[CH:33]=[CH:32][CH:31]=1)(=[O:29])=[O:28])([CH3:25])([CH3:23])[CH3:24]

Participants

3

Reactant 2

HCID 441195383-(tert-Butylaminosulphonyl)benzeneboronic acidHCID 574687612-(3-Bromo-phenyl)-4-(4-chloro-phenyl)-6-methyl-pyrimidine

Product 1

HCID 602094263'-[4-(4-Chloro-phenyl)-6-methyl-pyrimidin-2-yl]-biphenyl-3-sulfonic acid tert-butylamide

Procedure

3′-[4-(4-Chloro-phenyl)-6-methyl-pyrimidin-2-yl]-biphenyl-3-sulfonic acid tert-butylamide was prepared from 2-(3-bromo-phenyl)-4-(4-chloro-phenyl)-6-methyl-pyrimidine (example E.44) (0.11 g, 0.3 mmol) and commercially available 3-(tert.-butylsulfamoyl)-phenylboronic acid (0.09 g, 0.35 mmol) according to the general procedure VI. Obtained as a light brown solid (0.16 g), which was subsequently deprotected.

Sources & evidence

ORD record
ord-348cb51e6cf940efb9cd2b2d41b74308
Source dataset
uspto-grants-2012_05
Patent number
US08183262B2

Reaction notes

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