Sodium Carbonate → (E)-2-Chloro-4-(2-cyclohexyl-1-hydroxymethyl-vinyl)-benzenesulfonamide

HRID 2103600Notes

Reaction equation

HRID 2103600 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH2:11])(=[O:10])=[O:9])=[C:4]([Cl:12])[CH:3]=1.[CH:13]1(/[CH:19]=[C:20](\B2OC(C)(C)C(C)(C)O2)/[CH2:21][OH:22])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1.C(=O)([O-])[O-].[Na+].[Na+]>CN(C=O)C.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]>[Cl:12][C:4]1[CH:3]=[C:2](/[C:20](/[CH2:21][OH:22])=[CH:19]\[CH:13]2[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)[CH:7]=[CH:6][C:5]=1[S:8]([NH2:11])(=[O:10])=[O:9]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27347644-Bromo-2-chlorobenzenesulfonamideHCID 67084598(E)-3-cyclohexyl-2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-prop-2-en-1-ol

Product 1

HCID 67084477(E)-2-Chloro-4-(2-cyclohexyl-1-hydroxymethyl-vinyl)-benzenesulfonamideYield 109.8%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 6228DimethylformamideSolvent

Procedure

According to example 26b, reaction of 4-bromo-2-chloro-benzenesulfonamide (1.0 g, 3.7 mmol), dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium (II) dichloromethane adduct (271 mg, 0.37 mmol), (E)-3-cyclohexyl-2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-prop-2-en-1-ol (1.5 g, 5.5 mmol) and aqueous sodium carbonat solution (2 M, 3.60 mL, 7.40 mmol) in 15 mL DMF at 80° C. and purification via column chromatography on silica gel, eluting with a gradient from 70:30 to 50:50 hexane:ethyl acetate affords the title compound as an oil (1.34 g). MS (m/e): 312 [(M−H2O)+H].

Workup

  1. custompurification via column chromatography on silica gel
  2. washeluting with a gradient from 70:30 to 50:50 hexane

Sources & evidence

ORD record
ord-5a759fa633e345ecbbd421a9686375cb
Source dataset
uspto-grants-2009_08
Patent number
US07576108B2

Reaction notes

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