3-[6-Methyl-4-(4-trifluoromethyl-phenyl)pyridin-2-yl]-benzeneboronic acid → 5-{3-[6-Methyl-4-(4-trifluoromethyl-phenyl)-pyridin-2-yl]-phenyl}-pyridine-3-sulfonic acid (2-hydroxy-1,1-dimethyl-ethyl)-amide

HRID 1989564Notes

Reaction equation

HRID 1989564 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([C:8]2[CH:9]=[C:10](B(O)O)[CH:11]=[CH:12][CH:13]=2)[CH:5]=[C:4]([C:17]2[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][CH:18]=2)[CH:3]=1.[OH:27][CH2:28][C:29]([NH:32][S:33]([C:36]1[CH:37]=[N:38][CH:39]=[C:40](Br)[CH:41]=1)(=[O:35])=[O:34])([CH3:31])[CH3:30]>>[OH:27][CH2:28][C:29]([NH:32][S:33]([C:36]1[CH:37]=[N:38][CH:39]=[C:40]([C:10]2[CH:11]=[CH:12][CH:13]=[C:8]([C:6]3[CH:5]=[C:4]([C:17]4[CH:18]=[CH:19][C:20]([C:23]([F:25])([F:24])[F:26])=[CH:21][CH:22]=4)[CH:3]=[C:2]([CH3:1])[N:7]=3)[CH:9]=2)[CH:41]=1)(=[O:35])=[O:34])([CH3:31])[CH3:30]

Participants

3

Reactant 2

HCID 602093413-[6-Methyl-4-(4-trifluoromethyl-phenyl)pyridin-2-yl]-benzeneboronic acidHCID 602093435-bromo-N-(1-hydroxy-2-methylpropan-2-yl)pyridine-3-sulfonamide

Product 1

HCID 602094595-{3-[6-Methyl-4-(4-trifluoromethyl-phenyl)-pyridin-2-yl]-phenyl}-pyridine-3-sulfonic acid (2-hydroxy-1,1-dimethyl-ethyl)-amide

Procedure

The title compound was prepared from 3-[6-methyl-4-(4-trifluoromethyl-phenyl)-pyridin-2-yl]-benzeneboronic acid (example G.9) (0.20 g, 0.56 mmol) and 5-bromo-pyridine-3-sulfonic acid (2-hydroxy-1,1-dimethyl-ethyl)-amide (example H.2) (0.173 g, 0.56 mmol) according to the general procedure VI. Obtained as a white solid (0.080 g, 26%). MS (ISP) 542.2 [(M+H)+]; mp 105° C. (dec.).

Sources & evidence

ORD record
ord-3b7c15be06f5467396574a51e128b7f2
Source dataset
uspto-grants-2010_01
Patent number
US07642264B2

Reaction notes

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