1-Cyclohexenylboronic acid → 2-(4-Amino-3-cyclohex-1-enyl-phenyl)-ethanesulfonic acid tert-butylamide

HRID 1711290Notes

Reaction equation

HRID 1711290 reaction equation
[C:1]1(B(O)O)[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1.[C:10]([NH:14][S:15]([CH2:18][CH2:19][C:20]1[CH:25]=[CH:24][C:23]([NH2:26])=[C:22](Br)[CH:21]=1)(=[O:17])=[O:16])([CH3:13])([CH3:12])[CH3:11]>>[C:10]([NH:14][S:15]([CH2:18][CH2:19][C:20]1[CH:25]=[CH:24][C:23]([NH2:26])=[C:22]([C:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=2)[CH:21]=1)(=[O:17])=[O:16])([CH3:13])([CH3:12])[CH3:11]

Participants

3

Reactant 2

HCID 38629021-Cyclohexenylboronic acidHCID 587548332-(4-Amino-3-bromo-phenyl)-ethanesulfonic acid tert-butylamide

Product 1

HCID 587548162-(4-Amino-3-cyclohex-1-enyl-phenyl)-ethanesulfonic acid tert-butylamide

Procedure

The title compound was prepared according to the Suzuki coupling procedure of Example 44, step (b) using cyclohex-1-enyl boronic acid (117 mg, 0.931 mmol) and 2-(4-amino-3-bromo-phenyl)-ethanesulfonic acid tert-butylamide (as prepared in the previous step, 250 mg, 0.745 mmol) and purified on silica (20% EtOAc/hexanes) (228 mg, 91%). 1H-NMR (CDCl3; 400 MHz): δ 6.87 (dd, 1H, J=8.0, 2.1 Hz), 6.82 (d, 1H, J=2.1 Hz), 6.64 (d, 1H, J=8.0 Hz), 5.72 (br s, 1H), 4.12 (s, 1H), 3.82 (br s, 2H), 3.28 (m, 2H), 2.96 (m, 2H), 2.19-2.23 (m, 4H), 1.62-1.82 (m, 4H), 1.31 (s, 9H).

Workup

  1. customas prepared in the previous step, 250 mg, 0.745 mmol) and
  2. custompurified on silica (20% EtOAc/hexanes) (228 mg, 91%)

Sources & evidence

ORD record
ord-c0b8ba9040b2406a85cc79f7802f3aa8
Source dataset
uspto-grants-2010_09
Patent number
US07790724B2

Reaction notes

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