1-Cyclohexenylboronic acid → 4-Amino-3-cyclohex-1-enyl-benzamide

HRID 1711243Notes

Reaction equation

HRID 1711243 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH2:8])=[O:7])=[CH:4][C:3]=1Br.[C:12]1(B(O)O)[CH2:17][CH2:16][CH2:15][CH2:14][CH:13]=1>>[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH2:8])=[O:7])=[CH:4][C:3]=1[C:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH:13]=1

Participants

3

Reactant 2

HCID 38629021-Cyclohexenylboronic acidHCID 121180554-Amino-3-bromobenzamide

Product 1

HCID 587548054-Amino-3-cyclohex-1-enyl-benzamideYield 76%

Procedure

The title compound was prepared by the Suzuki coupling procedure of Example 11, step (e) using 4-amino-3-bromo-benzamide (as prepared in the previous step, 500 mg, 2.32 mmol), and cyclohexane-1-enyl boronic acid (322 mg, 2.56 mmol). The mixture was purified by trituration with DCM to afford the title compound (382 mg, 76%) as a yellow solid. Mass spectrum (ESI, m/z): Calcd. for C13H16N2O, 217.1 (M+H), found 217.2.

Workup

  1. customThe title compound was prepared by the Suzuki coupling procedure of Example 11, step (e)
  2. customThe mixture was purified by trituration with DCM

Sources & evidence

ORD record
ord-4d031e1517fe4fbeaa4aac973adb0c04
Source dataset
uspto-grants-2010_09
Patent number
US07790724B2

Reaction notes

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