Sodium Carbonate → (4-Amino-3-cyclohex-1-enyl-phenyl)-acetonitrile
Reaction equation
C[C:2]1(C)[CH2:7][CH2:6][C:5]([C:8]2[C:13]([N+]([O-])=O)=[CH:12][CH:11]=[CH:10][N:9]=2)=[CH:4][CH2:3]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>[NH2:9][C:8]1[CH:5]=[CH:4][C:12]([CH2:11][C:10]#[N:9])=[CH:13][C:8]=1[C:5]1[CH2:6][CH2:7][CH2:2][CH2:3][CH:4]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
The title compound was prepared from (4-amino-3-bromo-phenyl)-acetonitrile (as prepared in Example 42, step (a), 668 mg, 3.16 mmol), cyclohexen-yl pinacol boronic ester (790 mg, 3.79 mmol), Pd(PPh3)4 (365 mg, 0.31 mmol), and 2M Na2CO3 (15.2 mL, 12.6 mmol) according to the procedure in Example 44, step (b) (226 mg, 34%). 1H-NMR (CDCl3; 400 MHz): δ 6.88 (dd, 1H, J=8.1, 1.9 Hz), 6.84 (d, 1H, J=1.9 Hz), 6.58 (d, 1H, J=8.1 Hz), 5.67 (m, 1H), 3.73 (br s, 2H), 3.53 (s, 2H), 2.14-2.08 (m, 4H), 1.72-1.58 (m, 4H).