4,4-Dimethylcyclohexen-1-ylboronic acid → 1-[4-Amino-3-(4,4-dimethyl-cyclohex-1-enyl)-phenyl]-cyclopropanecarbonitrile

HRID 2408502Notes

Reaction equation

HRID 2408502 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:11]#[N:12])[CH2:10][CH2:9]2)=[CH:4][C:3]=1Br.[CH3:14][C:15]1([CH3:24])[CH2:20][CH2:19][C:18](B(O)O)=[CH:17][CH2:16]1>>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:11]#[N:12])[CH2:10][CH2:9]2)=[CH:4][C:3]=1[C:18]1[CH2:19][CH2:20][C:15]([CH3:24])([CH3:14])[CH2:16][CH:17]=1

Participants

3

Reactant 2

HCID 441195554,4-Dimethylcyclohexen-1-ylboronic acidHCID 688382611-(4-Amino-3-bromo-phenyl)-cyclopropanecarbonitrile

Product 1

HCID 589937611-[4-Amino-3-(4,4-dimethyl-cyclohex-1-enyl)-phenyl]-cyclopropanecarbonitrile

Procedure

The title compound was prepared from 1-(4-amino-3-bromo-phenyl)-cyclopropanecarbonitrile (as prepared in this step) and 4,4-dimethylcyclohexen-1-yl boronic acid using the conditions described in Example 1, step (e). 1H NMR (CD3OD; 400 MHz): δ 6.95 (dd, 1H, J=8.2, 2.3 Hz), 6.88 (d, 1H, J=2.3 Hz,), 6.71 (d, 1H, J=8.2 Hz), 5.62 (m, 1H), 2.52-2.23 (m, 2H), 1.98-1.97 (m, 2H), 1.55-1.51 (m, 4H), 1.31-1.28 (m, 2H), 1.01 (s, 6H).

Sources & evidence

ORD record
ord-39e7e8bbe96246ba9ecacdbff63862d4
Source dataset
uspto-grants-2014_08
Patent number
US08815867B2

Reaction notes

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