Sodium Carbonate → 2-chloro-N-(3-fluoro-3'-methanesulfonyl-biphenyl-4-ylmethyl)-N-isobutyl-benzenesulfonamide

HRID 1665062Notes

Reaction equation

HRID 1665062 reaction equation
Br[C:2]1[CH:23]=[CH:22][C:5]([CH2:6][N:7]([CH2:18][CH:19]([CH3:21])[CH3:20])[S:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[Cl:17])(=[O:10])=[O:9])=[C:4]([F:24])[CH:3]=1.[CH3:25][S:26]([C:29]1[CH:30]=[C:31](B(O)O)[CH:32]=[CH:33][CH:34]=1)(=[O:28])=[O:27].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:17][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1[S:8]([N:7]([CH2:6][C:5]1[CH:22]=[CH:23][C:2]([C:33]2[CH:32]=[CH:31][CH:30]=[C:29]([S:26]([CH3:25])(=[O:28])=[O:27])[CH:34]=2)=[CH:3][C:4]=1[F:24])[CH2:18][CH:19]([CH3:21])[CH3:20])(=[O:10])=[O:9]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27735423-(Methylsulfonyl)phenylboronic acidHCID 67441654N-(4-bromo-2-fluoro-benzyl)-2-chloro-N-isobutyl-benzenesulfonamide

Product 1

HCID 252343102-chloro-N-(3-fluoro-3'-methanesulfonyl-biphenyl-4-ylmethyl)-N-isobutyl-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-(4-bromo-2-fluoro-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-(3-fluoro-3′-methanesulfonyl-biphenyl-4-ylmethyl)-N-isobutyl-benzenesulfonamide as a colorless solid. MS: 568.2 ([M+OAc]−)

Sources & evidence

ORD record
ord-fa5d1994effe439b87a5b4a05ab8e8db
Source dataset
uspto-grants-2011_10
Patent number
US08039493B2

Reaction notes

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