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Potassium Phosphate, Tribasic → 4'-Amino-5'-methoxy-N,2'-dimethylbiphenyl-4-carboxamide

HRID 2091950
Notes
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Reaction equation

HRID 2091950 reaction equation
Cl[C:2]1[C:8]([CH3:9])=[CH:7][C:5]([NH2:6])=[C:4]([O:10][CH3:11])[CH:3]=1.[CH3:12][NH:13][C:14]([C:16]1[CH:21]=[CH:20][C:19](B(O)O)=[CH:18][CH:17]=1)=[O:15].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>C(O)CCC.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]>[NH2:6][C:5]1[C:4]([O:10][CH3:11])=[CH:3][C:2]([C:19]2[CH:20]=[CH:21][C:16]([C:14]([NH:13][CH3:12])=[O:15])=[CH:17][CH:18]=2)=[C:8]([CH3:9])[CH:7]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 807824-Chloro-5-methyl-o-anisidineHCID 27735264-(Methylcarbamoyl)benzeneboronic acidHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl

Product 1

HCID 595867914'-Amino-5'-methoxy-N,2'-dimethylbiphenyl-4-carboxamide

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst
HCID 2631-ButanolSolvent

Conditions

Temperature
130 °C

Procedure

The mixture of 4-chloro-2-methoxy-5-methylaniline (2.0 g, 11.7 mmol), 4-(methylcarbamoyl)phenylboronic acid (2.08 g, 11.7 mmol), 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (1.20 g, 2.9 mmol), Pd2(dba)3 (1.1 g, 1.2 mmol), and K3PO4 (7.4 g, 34.9 mmol) in 80 mL of n-butanol is degassed and heated at 130° C. overnight. The reaction mixture is filtered through a pad of celite, and concentrated in vacuo. The crude product mixture is partitioned between EtOAc and brine, the collected organic extracts are dried (Na2SO4), concentrated, and purified by silica gel chromatography (EtOAc/Hexanes:1/4) to afford 4′-Amino-5′-methoxy-N,2′-dimethylbiphenyl-4-carboxamide; ESMS m/z 271.1 (M+H+).

Workup

  1. customis degassed
  2. filtrationThe reaction mixture is filtered through a pad of celite
  3. concentrationconcentrated in vacuo
  4. customThe crude product mixture is partitioned between EtOAc and brine
  5. dry with materialthe collected organic extracts are dried (Na2SO4)
  6. concentrationconcentrated
  7. custompurified by silica gel chromatography (EtOAc/Hexanes:1/4)

Sources & evidence

ORD record
ord-ea0f7abac9e943299b314cdd1ce31e0e
Source dataset
uspto-grants-2013_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08440681B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes