Potassium Phosphate, Tribasic → 3-Amino-2'methoxy-4-nitro-biphenyl-2-carbonitrile

HRID 2421910Notes

Reaction equation

[NH2:1][C:2]1[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][CH:7]=[C:6](Cl)[C:3]=1[C:4]#[N:5].[CH3:14][O:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1B(O)O.P([O-])([O-])([O-])=O.[K+].[K+].[K+].C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2N(C)C)CCCCC1>CC(N(C)C)=O.CCOC(C)=O.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[NH2:1][C:2]1[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][CH:7]=[C:6]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[O:15][CH3:14])[C:3]=1[C:4]#[N:5]

Participants

Conditions

Temperature: 68 °C

Procedure

2-Amino-6-chloro-3-nitro-benzonitrile (see Goldberg et al., J. Med. Chem., 2003, 1344; 800 mg, 4.05 mmol), 2-methoxyphenylboronic acid (800 mg, 5.26 mmol), and potassium phosphate (2.23 g, 10.5 mmol) were combined in DMA (10 mL) in a flask purged with nitrogen. Tris(dibenzylideneacetone)dipalladium(0) (185 mg, 0.2 mmol) and 2-dicyclohexylphosphino-2′-(N,N-dimethyl-amino)biphenyl (159 mg, 0.4 mmol) were added, and the reaction stirred at 68° C. under nitrogen for 16 h. The solution was diluted with EtOAc (50 mL), and washed with 1N HCl and brine. Organics were dried (MgSO4) and concentrated in vacuo.

Workup

custompurged with nitrogen
washwashed with 1N HCl and brine
dry with materialOrganics were dried (MgSO4)
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-f8f10a1a9426402cbc48ea4a8a7ba560
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07960384B2

Reaction notes

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