(Pyridin-4-yl)boronic acid → 5-Fluoro-3-isobutyl-benzo[b]thiophene-2-sulfonic acid (4-pyridin-4-yl-2-trifluoromethyl-phenyl)-amide

HRID 1693140Notes

Reaction equation

HRID 1693140 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[CH2:22][CH:23]([CH3:25])[CH3:24])(=[O:11])=[O:10])=[C:4]([C:26]([F:29])([F:28])[F:27])[CH:3]=1.[N:30]1[CH:35]=[CH:34][C:33](B(O)O)=[CH:32][CH:31]=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:30]1[CH:35]=[CH:34][C:33]([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[CH2:22][CH:23]([CH3:25])[CH3:24])(=[O:10])=[O:11])=[C:4]([C:26]([F:29])([F:27])[F:28])[CH:3]=2)=[CH:32][CH:31]=1

Participants

7

Reactant 2

HCID 2734379(Pyridin-4-yl)boronic acidHCID 597599705-Fluoro-3-isobutyl-benzo[b]thiophene-2-sulfonic acid(4-bromo-2-trifluoromethyl-phenyl)-amide

Product 1

HCID 249670425-Fluoro-3-isobutyl-benzo[b]thiophene-2-sulfonic acid (4-pyridin-4-yl-2-trifluoromethyl-phenyl)-amideYield 471.7%

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-isobutyl-benzo[b]thiophene-2-sulfonic acid(4-bromo-2-trifluoromethyl-phenyl)-amide (0.10 g) and 4-pyridineboronic acid (0.036 g) in 1,2-dimethoxyethane (7 ml), ethanol (1 ml) and 2 molar sodium carbonate (2.0 ml) with tetrakis(triphenylphosphine)palladium (0.027 g) to obtain the title compound (0.47 g) as a yellowish solid. MS (ISN): 507.1 (M−H)−

Sources & evidence

ORD record
ord-b192062951bc448abf9c4b9a9b0d4206
Source dataset
uspto-grants-2012_04
Patent number
US08158655B2

Reaction notes

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