1-Cyclohexenylboronic acid → 4-amino-N-tert-butyl-3-cyclohex-1-enyl-benzenesulfonamide

HRID 1711294Notes

Reaction equation

HRID 1711294 reaction equation
[C:1]1(B(O)O)[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1.[NH2:10][C:11]1[CH:16]=[CH:15][C:14]([S:17]([NH:20][C:21]([CH3:24])([CH3:23])[CH3:22])(=[O:19])=[O:18])=[CH:13][C:12]=1Br>>[NH2:10][C:11]1[CH:16]=[CH:15][C:14]([S:17]([NH:20][C:21]([CH3:24])([CH3:23])[CH3:22])(=[O:19])=[O:18])=[CH:13][C:12]=1[C:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1

Participants

3

Reactant 2

HCID 38629021-Cyclohexenylboronic acidHCID 548502844-amino-3-bromo-N-tert-butyl-benzenesulfonamide

Product 1

HCID 587548594-amino-N-tert-butyl-3-cyclohex-1-enyl-benzenesulfonamideYield 70.5%

Procedure

4-Amino-N-tert-butyl-3-cyclohex-1-enyl-benzenesulfonamide was prepared according to the Suzuki coupling procedure of Example 44, step (b) using cyclohex-1-enyl boronic acid (63 mg, 0.50 mmol) and 4-amino-3-bromo-N-tert-butyl-benzenesulfonamide (123 mg, 0.400 mmol, as prepared above) to obtain 4-amino-N-tert-butyl-3-cyclohex-1-enyl-benzenesulfonamide (87 mg, 70%) after purification on silica (30% EtOAc/hexanes). Mass spectrum (ESI, m/z): Calcd. for C16H24N2O2S, 309.1 (M+H), found 309.1

Workup

  1. custom4-Amino-N-tert-butyl-3-cyclohex-1-enyl-benzenesulfonamide was prepared

Sources & evidence

ORD record
ord-d520a9413a6944a0a329047d91f5abdb
Source dataset
uspto-grants-2010_09
Patent number
US07790724B2

Reaction notes

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