Sodium Carbonate → (4-Amino-3-cyclohex-1-enyl-phenyl)-acetonitrile

HRID 1711311Notes

Reaction equation

HRID 1711311 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]=1

Participants

4

Reactant 2

HCID 10340Sodium CarbonateHCID 685051192-(4,4-Dimethyl-cyclohex-1-enyl)-3-nitro-pyridine

Product 1

HCID 58754819(4-Amino-3-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 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).

Sources & evidence

ORD record
ord-a9cfe46773fc4a32834e181ceedea018
Source dataset
uspto-grants-2010_09
Patent number
US07790724B2

Reaction notes

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