(Pyrimidin-5-yl)boronic acid → 5-Fluoro-3-methyl-benzo[b]thiophene-2-sulfonic acid (4-pyrimidin-5-yl-2-trifluoromethyl-phenyl)-amide

HRID 1693103Notes

Reaction equation

HRID 1693103 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([NH:8][S:9]([C:12]2[S:16][C:15]3[CH:17]=[CH:18][C:19]([F:21])=[CH:20][C:14]=3[C:13]=2[CH3:22])(=[O:11])=[O:10])=[C:4]([C:23]([F:26])([F:25])[F:24])[CH:3]=1.[N:27]1[CH:32]=[C:31](B(O)O)[CH:30]=[N:29][CH:28]=1>COCCOC.C(O)C.C(=O)([O-])[O-].[Na+].[Na+].C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[N:27]1[CH:32]=[C:31]([C:2]2[CH:7]=[CH:6][C:5]([NH:8][S:9]([C:12]3[S:16][C:15]4[CH:17]=[CH:18][C:19]([F:21])=[CH:20][C:14]=4[C:13]=3[CH3:22])(=[O:11])=[O:10])=[C:4]([C:23]([F:24])([F:25])[F:26])[CH:3]=2)[CH:30]=[N:29][CH:28]=1

Participants

7

Reactant 2

HCID 2795193(Pyrimidin-5-yl)boronic acidHCID 249652745-Fluoro-3-methyl-benzo[b]thiophene-2-sulfonic acid(4-bromo-2-trifluoromethyl-phenyl)-amide

Product 1

HCID 249659695-Fluoro-3-methyl-benzo[b]thiophene-2-sulfonic acid (4-pyrimidin-5-yl-2-trifluoromethyl-phenyl)-amideYield 45.1%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 80711,2-DimethoxyethaneSolventHCID 10340Sodium CarbonateSolvent

Procedure

This compound was prepared in analogy to Example 2 starting from 5-fluoro-3-methyl-benzo[b]thiophene-2-sulfonic acid(4-bromo-2-trifluoromethyl-phenyl)-amide (0.10 g) and pyrimidine-5-boronic acid (0.053 g) in 1,2-dimethoxyethane (1.5 ml), ethanol (0.32 ml) and 2 M aqueous sodium carbonate solution (0.8 ml) with tetrakis(triphenylphosphine)palladium (0.012 g) to obtain the title compound (0.045 g) as a colorless solid. MS (ISN): 466.1 (M−H)−

Sources & evidence

ORD record
ord-420bf23562c04eecaa912e5791c8ade8
Source dataset
uspto-grants-2012_04
Patent number
US08158655B2

Reaction notes

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