Sodium Carbonate → 2-chloro-N-isobutyl-N-[5-(3-methanesulfonyl-phenyl)-pyridin-2-ylmethyl]-benzenesulfonamide

HRID 1665068Notes

Reaction equation

HRID 1665068 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([CH2:8][N:9]([CH2:20][CH:21]([CH3:23])[CH3:22])[S:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[Cl:19])(=[O:12])=[O:11])=[N:6][CH:7]=1.[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:19][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[S:10]([N:9]([CH2:20][CH:21]([CH3:23])[CH3:22])[CH2:8][C:5]1[CH:4]=[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:7][N:6]=1)(=[O:12])=[O:11]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27735423-(Methylsulfonyl)phenylboronic acidHCID 67439287N-(5-bromo-pyridin-2-ylmethyl)-2-chloro-N-isobutyl-benzenesulfonamide

Product 1

HCID 252343132-chloro-N-isobutyl-N-[5-(3-methanesulfonyl-phenyl)-pyridin-2-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-(5-bromo-pyridin-2-ylmethyl)-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-[5-(3-methanesulfonyl-phenyl)-pyridin-2-ylmethyl]-benzenesulfonamide as a colorless solid. MS: 493.0 ([M+H]+)

Sources & evidence

ORD record
ord-326aef7ff56540c7be09454e84572cd9
Source dataset
uspto-grants-2011_10
Patent number
US08039493B2

Reaction notes

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