Sodium Carbonate → HCID 68509947, compound

HRID 1711315Notes

Reaction equation

HRID 1711315 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1Br.[CH3:11][C:12]1([CH3:21])[CH2:17][CH2:16][C:15](B(O)O)=[CH:14][CH2:13]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:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[C:15]1[CH2:16][CH2:17][C:12]([CH3:21])([CH3:11])[CH2:13][CH:14]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 15152794-Amino-3-bromobenzonitrileHCID 441195554,4-Dimethylcyclohexen-1-ylboronic acid

Product 1

HCID 68509947HCID 68509947, compound

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Procedure

The title compound was prepared from 4-amino-3-bromo-benzonitrile (as prepared in the previous step, 1.0 g, 5.0 mmol), 4,4-dimethylcyclohexen-1-yl boronic acid (938 mg, 6.07 mmol), Pd(PPh3)4 (585 mg, 0.506 mmol) and 2M Na2CO3 (20.2 mL, 40.5 mmol) according to the procedure in Example 44, step (b) (284 mg, 25%). Mass spectrum (ESI, m/z): Calcd. for C15H18N2, 227.1, found 227.3.

Sources & evidence

ORD record
ord-41be82c366084d60aa97caf84797bba4
Source dataset
uspto-grants-2010_09
Patent number
US07790724B2

Reaction notes

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