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

HRID 2421910
Notes
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Reaction equation

HRID 2421910 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 27339582-Methoxyphenylboronic acidHCID 27342172-(Dicyclohexylphosphino)-2'-(dimethylamino)biphenylHCID 112756272-Amino-6-chloro-3-nitro-benzonitrile

Product 1

HCID 252418023-Amino-2'methoxy-4-nitro-biphenyl-2-carbonitrile

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst
HCID 8857Ethyl AcetateSolvent
HCID 31374DimethylacetamideSolvent

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

  1. custompurged with nitrogen
  2. washwashed with 1N HCl and brine
  3. dry with materialOrganics were dried (MgSO4)
  4. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes