(Pyridin-4-yl)boronic acid → HCID 24966317, compound

HRID 1693112Notes

Reaction equation

HRID 1693112 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]([CH2:23][CH3:24])[CH:3]=1.[N:25]1[CH:30]=[CH:29][C:28](B(O)O)=[CH:27][CH:26]=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>[CH2:23]([C:4]1[CH:3]=[C:2]([C:28]2[CH:29]=[CH:30][N:25]=[CH:26][CH:27]=2)[CH:7]=[CH:6][C:5]=1[NH:8][S:9]([C:12]1[S:16][C:15]2[CH:17]=[CH:18][C:19]([F:21])=[CH:20][C:14]=2[C:13]=1[CH3:22])(=[O:10])=[O:11])[CH3:24]

Participants

7

Reactant 2

HCID 2734379(Pyridin-4-yl)boronic acidHCID 59759963HCID 59759963, compound

Product 1

HCID 24966317HCID 24966317, compoundYield 25.1%

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-3-methyl-benzo[b]thiophene-2-sulfonic acid(4-bromo-2-ethyl-phenyl)-amide (0.10 g) and 4-pyridineboronic acid (0.043 g) in 1,2-dimethoxyethane (1.5 ml), ethanol (0.25 ml) and 2 M aqueous sodium carbonate solution (0.9 ml) with tetrakis(triphenylphosphine)palladium (0.013 g) to obtain the title compound (0.025 g) as a yellowish foam. MS (ISP): 427.3 (M+H)+

Sources & evidence

ORD record
ord-95f56b06650f41d7a8490401c17f5c54
Source dataset
uspto-grants-2012_04
Patent number
US08158655B2

Reaction notes

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