(Pyridin-4-yl)boronic acid → HCID 24966316, compound

HRID 1693110Notes

Reaction equation

HRID 1693110 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][S:24]([CH3:27])(=[O:26])=[O: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>[CH3:27][S:24]([CH2:23][C:4]1[CH:3]=[C:2]([C:31]2[CH:32]=[CH:33][N:28]=[CH:29][CH:30]=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:11])=[O:10])(=[O:26])=[O:25]

Participants

7

Reactant 2

HCID 2734379(Pyridin-4-yl)boronic acidHCID 59759977HCID 59759977, compound

Product 1

HCID 24966316HCID 24966316, compoundYield 23.7%

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-methyl-benzo[b]thiophene-2-sulfonic acid(4-bromo-2-methanesulfonylmethyl-phenyl)-amide (0.123 g) and 4-pyridineboronic acid (0.0462 g) in 1,2-dimethoxyethane (5 ml), ethanol (1 ml) and 2 M aqueous sodium carbonate solution (2 ml) with tetrakis(triphenylphosphine)palladium (0.035 g) to obtain the title compound (0.029 g) as a yellowish foam. MS (ISN): 489.1 (M−H)−

Sources & evidence

ORD record
ord-7c606df5d8d442fb8061be3844ad6731
Source dataset
uspto-grants-2012_04
Patent number
US08158655B2

Reaction notes

Loading…