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Sodium Carbonate → 2,4'-Dimethyl-[1,1'-biphenyl]-3-amine

HRID 1269651
Notes
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Reaction equation

HRID 1269651 reaction equation
Br[C:2]1[C:3]([CH3:9])=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].[CH3:10][C:11]1[CH:16]=[CH:15][C:14](B(O)O)=[CH:13][CH:12]=1.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.O.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:9][C:3]1[C:4]([NH2:5])=[CH:6][CH:7]=[CH:8][C:2]=1[C:14]1[CH:15]=[CH:16][C:11]([CH3:10])=[CH:12][CH:13]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 79799Tolylboronic acidHCID 1235383-Bromo-o-toluidine

Product 1

HCID 184483212,4'-Dimethyl-[1,1'-biphenyl]-3-amineYield 93%

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalyst
HCID 962
Water
Solvent
HCID 80711,2-DimethoxyethaneSolvent

Procedure

To a solution of 3-bromo-2-methylaniline (15 g, 0.0806 mol) in 1,2-dimethoxyethane (330 ml) and water (165 ml) was added 4-methylphenylboronic acid (12.05 g, 0.0886 mol) and sodium carbonate (22.2 g, 0.2095 mol). The apparatus was flushed with nitrogen prior to the addition of tetrakis(triphenylphosphine) palladium (0) (1.86 g, 1.61 mmol). The resultant mixture was heated at 90° C. and stirred under nitrogen for 22 h, then allowed to cool to room temperature and the solvents removed in vacuo. The residue was partitioned between EtOAc (2×400 ml) and water (400 ml). The organic solution was dried (Na2SO4) and the solvent was removed in vacuo. Purification by Biotage™ chromatography (4×90 g Si column) eluted with 9:1 to 8:1 EtOAc:cyclohexane afforded the title compound as a yellow oil (14.78 g).

Workup

  1. customThe apparatus was flushed with nitrogen
  2. customthe solvents removed in vacuo
  3. customThe residue was partitioned between EtOAc (2×400 ml) and water (400 ml)
  4. dry with materialThe organic solution was dried (Na2SO4)
  5. customthe solvent was removed in vacuo
  6. customPurification by Biotage™ chromatography (4×90 g Si column)
  7. washeluted with 9:1 to 8:1 EtOAc

Sources & evidence

ORD record
ord-e5c7371ed1fd42a8bc3deed1356c6a38
Source dataset
uspto-grants-2007_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07199239B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes