Sodium Carbonate → 2-chloro-N-isobutyl-N-[4-(3-tert-butylaminosulfonyl-phenyl)-thiophen-2-ylmethyl]-benzenesulfonamide

HRID 1665083Notes

Reaction equation

HRID 1665083 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH2:7][N:8]([CH2:19][CH:20]([CH3:22])[CH3:21])[S:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[Cl:18])(=[O:11])=[O:10])[S:5][CH:6]=1.[C:23]([NH:27][S:28]([C:31]1[CH:32]=[C:33](B(O)O)[CH:34]=[CH:35][CH:36]=1)(=[O:30])=[O:29])([CH3:26])([CH3:25])[CH3:24].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:18][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[S:9]([N:8]([CH2:19][CH:20]([CH3:22])[CH3:21])[CH2:7][C:4]1[S:5][CH:6]=[C:2]([C:33]2[CH:34]=[CH:35][CH:36]=[C:31]([S:28]([NH:27][C:23]([CH3:26])([CH3:25])[CH3:24])(=[O:29])=[O:30])[CH:32]=2)[CH:3]=1)(=[O:11])=[O:10]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 441195383-(tert-Butylaminosulphonyl)benzeneboronic acidHCID 67439155N-(4-bromo-thiophen-2-ylmethyl)-2-chloro-N-isobutyl-benzenesulfonamide

Product 1

HCID 252343232-chloro-N-isobutyl-N-[4-(3-tert-butylaminosulfonyl-phenyl)-thiophen-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-(4-bromo-thiophen-2-ylmethyl)-2-chloro-N-isobutyl-benzenesulfonamide (example 14, step 2) was reacted with 3-tert-butylsulfamoyl-benzeneboronic acid (CAS [221290-14-8]), Na2CO3 and dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium dichloromethane adduct in dioxane/water to give 2-chloro-N-isobutyl-N-[4-(3-tert-butylaminosulfonyl-phenyl)-thiophen-2-ylmethyl]-benzenesulfonamide as an off-white solid. MS: 553.6 ([M−H]−)

Sources & evidence

ORD record
ord-5de21a3ed28247ac8a2788d5ef48e02d
Source dataset
uspto-grants-2011_10
Patent number
US08039493B2

Reaction notes

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