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

HRID 1693097Notes

Reaction equation

HRID 1693097 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]=[CH:31][C:30](B(O)O)=[CH:29][CH:28]=1>COCCOC.C(O)C.C(=O)([O-])[O-].[Na+].[Na+]>[N:27]1[CH:32]=[CH:31][C:30]([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:10])=[O:11])=[C:4]([C:23]([F:26])([F:24])[F:25])[CH:3]=2)=[CH:29][CH:28]=1

Participants

6

Reactant 2

HCID 2734379(Pyridin-4-yl)boronic acidHCID 249652745-Fluoro-3-methyl-benzo[b]thiophene-2-sulfonic acid(4-bromo-2-trifluoromethyl-phenyl)-amide

Product 1

HCID 249656235-Fluoro-3-methyl-benzo[b]thiophene-2-sulfonic acid(4-pyridin-4-yl-2-trifluoromethyl-phenyl)-amideYield 70.3%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 80711,2-DimethoxyethaneSolventHCID 10340Sodium CarbonateSolvent

Conditions

Temperature
80 °C

Procedure

A suspension of 5-fluoro-3-methyl-benzo[b]thiophene-2-sulfonic acid(4-bromo-2-trifluoromethyl-phenyl)-amide (0.5 g) and 4-pyridineboronic acid (0.197 g) in 1,2-dimethoxyethane (6 ml), ethanol (2 ml) and 2 M aqueous sodium carbonate solution (4.0 ml) was degassed 3-4 times to remove oxygen, then tetrakis(triphenylphosphine)palladium (0.065 g) was added. The reaction mixture was stirred at 80° C. for 3 h, quenched with ice/water, and extracted with ethyl acetate. The organic layers were washed, dried and concentrated. The residue was chromatographed over silica gel using heptane/ethyl acetate as eluent to obtain the title compound (0.35 g) as a yellowish solid. MS (ISP): 467.3 (M+H)+

Workup

  1. customwas degassed 3-4 times
  2. customto remove oxygen
  3. additiontetrakis(triphenylphosphine)palladium (0.065 g) was added
  4. customquenched with ice/water
  5. extractionextracted with ethyl acetate
  6. washThe organic layers were washed
  7. customdried
  8. concentrationconcentrated
  9. customThe residue was chromatographed over silica gel

Sources & evidence

ORD record
ord-24ac4c2bd64d48e18134f96aba296de2
Source dataset
uspto-grants-2012_04
Patent number
US08158655B2

Reaction notes

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