(Pyridin-4-yl)boronic acid → HCID 24967041, compound

HRID 1693136Notes

Reaction equation

HRID 1693136 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([NH:8][S:9]([C:12]2[N:13]([CH3:23])[C:14]3[C:19]([C:20]=2[CH3:21])=[CH:18][C:17]([F:22])=[CH:16][CH:15]=3)(=[O:11])=[O:10])=[C:4]([C:24]([F:27])([F:26])[F:25])[CH:3]=1.[N:28]1[CH:33]=[CH:32][C:31](B(O)O)=[CH:30][CH:29]=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:28]1[CH:33]=[CH:32][C:31]([C:2]2[CH:7]=[CH:6][C:5]([NH:8][S:9]([C:12]3[N:13]([CH3:23])[C:14]4[C:19]([C:20]=3[CH3:21])=[CH:18][C:17]([F:22])=[CH:16][CH:15]=4)(=[O:11])=[O:10])=[C:4]([C:24]([F:25])([F:27])[F:26])[CH:3]=2)=[CH:30][CH:29]=1

Participants

7

Reactant 2

HCID 2734379(Pyridin-4-yl)boronic acidHCID 59759973HCID 59759973, compound

Product 1

HCID 24967041HCID 24967041, compoundYield 58.2%

Reagents, catalysts & solvents 4

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

Procedure

This product was prepared in analogy to Example 2 starting from 5-fluoro-1,3-dimethyl-1H-indole-2-sulfonic acid(4-bromo-2-trifluoromethyl-phenyl)-amide (0.100 g), 4-pyridineboronic acid (0.040 g) in 1,2-dimethoxyethane (5.0 ml), ethanol (1.0 ml) and 2 M aqueous sodium carbonate solution (1.0 ml) with tetrakis(triphenylphosphine)palladium (0.025 g) to obtain the title compound (0.058 g) as a brownish foam. MS (ISN): 462.4 (M−H)−

Sources & evidence

ORD record
ord-80438754161b4d39838bb628b1ea2187
Source dataset
uspto-grants-2012_04
Patent number
US08158655B2

Reaction notes

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