Sodium Carbonate → [4-Amino-3-(4,4-dimethyl-cyclohex-1-enyl)-phenyl]-acetonitrile

HRID 1711307Notes

Reaction equation

HRID 1711307 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]#[N:10])=[CH:4][C:3]=1Br.[CH3:12][C:13]1([CH3:22])[CH2:18][CH2:17][C:16](B(O)O)=[CH:15][CH2:14]1.C([O-])([O-])=O.[Na+].[Na+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]#[N:10])=[CH:4][C:3]=1[C:16]1[CH2:17][CH2:18][C:13]([CH3:22])([CH3:12])[CH2:14][CH:15]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 441195554,4-Dimethylcyclohexen-1-ylboronic acidHCID 45037053(4-Amino-3-bromophenyl)acetonitrile

Product 1

HCID 58754882[4-Amino-3-(4,4-dimethyl-cyclohex-1-enyl)-phenyl]-acetonitrile

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Procedure

The title compound was prepared from (4-amino-3-bromo-phenyl)-acetonitrile (as prepared in the previous step, 805 mg, 3.81 mmol), 4,4-dimethylcyclohexen-1-yl boronic acid (705 mg, 4.57 mmol), Pd(PPh3)4 (440 mg, 0.380 mmol), and 2M Na2CO3 (15.2 mL, 30.5 mmol) according to the procedure in Example 34, step (b) (417 mg, 46%). 1H—NMR (CDCl3; 400 MHz): δ 6.89 (1H, dd, J=8.1, 2.0 Hz), 6.84 (1H, d, J=2.0 Hz), 6.59 (d, 1H, J=8.1 Hz), 5.60 (m, 1H), 3.71 (br s, 2H), 2.19-2.15 (m, 2H), 1.90-1.88 (m, 2H), 1.45-1.42 (m, 2H), 0.92 (s, 6H).

Sources & evidence

ORD record
ord-96aa3cf119a54781a405778032a7932a
Source dataset
uspto-grants-2010_09
Patent number
US07790724B2

Reaction notes

Loading…