Sodium Carbonate → 2-chloro-N-isobutyl-N-(3'-methanesulfonyl-biphenyl-3-ylmethyl)-benzenesulfonamide

HRID 1665064Notes

Reaction equation

HRID 1665064 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:21]=[CH:22][CH:23]=1)[CH2:5][N:6]([CH2:17][CH:18]([CH3:20])[CH3:19])[S:7]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[Cl:16])(=[O:9])=[O:8].[CH3:24][S:25]([C:28]1[CH:29]=[C:30](B(O)O)[CH:31]=[CH:32][CH:33]=1)(=[O:27])=[O:26].C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].ClCCl>[Cl:16][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=1[S:7]([N:6]([CH2:17][CH:18]([CH3:20])[CH3:19])[CH2:5][C:4]1[CH:3]=[C:2]([C:32]2[CH:31]=[CH:30][CH:29]=[C:28]([S:25]([CH3:24])(=[O:27])=[O:26])[CH:33]=2)[CH:23]=[CH:22][CH:21]=1)(=[O:9])=[O:8]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27735423-(Methylsulfonyl)phenylboronic acidHCID 67441490N-(3-bromo-benzyl)-2-chloro-N-isobutyl-benzenesulfonamide

Product 1

HCID 252343112-chloro-N-isobutyl-N-(3'-methanesulfonyl-biphenyl-3-ylmethyl)-benzenesulfonamide

Reagents, catalysts & solvents 2

HCID 178418807HCID 178418807, compoundCatalystHCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

In analogy to example 1, step 3, N-(3-bromo-benzyl)-2-chloro-N-isobutyl-benzenesulfonamide was reacted with (3-methylsulfonylphenyl)-boronic acid, Na2CO3 and dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium dichloromethane adduct in dioxane/water to give 2-chloro-N-isobutyl-N-(3′-methanesulfonyl-biphenyl-3-ylmethyl)-benzenesulfonamide as a colorless solid. MS: 550.2 ([M+OAc]−)

Sources & evidence

ORD record
ord-fa3ad884bc0545b482ca4eab2fddc203
Source dataset
uspto-grants-2011_10
Patent number
US08039493B2

Reaction notes

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