Cesium carbonate → Methyl 5'-amino-2'-methyl-1,1'-biphenyl-4-carboxylate

HRID 859795Notes

Reaction equation

BrC1C=C(C=CC=1C)N.[NH2:10][C:11]1[CH:12]=[CH:13][C:14]([CH3:27])=[C:15]([C:17]2[CH:22]=[CH:21][C:20]([C:23]([O:25][CH3:26])=[O:24])=[CH:19][CH:18]=2)[CH:16]=1.COC(C1C=CC(B(O)O)=CC=1)=O.C(=O)([O-])[O-].[Cs+].[Cs+]>COCCOC.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>[NH2:10][C:11]1[CH:12]=[CH:13][C:14]([CH3:27])=[C:15]([C:17]2[CH:22]=[CH:21][C:20]([C:23]([O:25][CH3:26])=[O:24])=[CH:19][CH:18]=2)[CH:16]=1

Participants

Conditions

Temperature: 90 °C

Procedure

Methyl 5′-amino-2′-methyl-1,1′-biphenyl-4-carboxylate 3-Bromo-4-methylaniline (744 mg, 4.0 mmol), (4-methoxycarbonylphenyl)boronic acid (864 mg, 4.8 mmol), tetrakis(triphenylphosphine)palladium (100 mg, 0.087 mmol) and caesium carbonate (2.4 g, 7.37 mmol) were mixed in DME (30 ml) and heated at 90° C. for 20 h. The reaction was absorbed onto silica applied to a silica SPE (10 g) and eluted with ethyl acetate/cyclohexane (0–100% ethyl acetate). The solvent was evaporated from the product fractions under vacuum to give methyl 5′-amino-2′-methyl-1,1′-biphenyl-4-carboxylate (500 mg, 43%). NMR; δH CDCl3 8.07,(2H, d), 7.38,(2H, d), 7.07,(1H, d), 6.67,(1H, dd), 6.60,(1H, d), 3.94,(3H, s), 2.14,(3H, s).

Workup

customThe reaction was absorbed onto silica
washeluted with ethyl acetate/cyclohexane (0–100% ethyl acetate)
customThe solvent was evaporated from the product fractions under vacuum

Sources & evidence

ORD record: ord-4eba057983bf49d59a3d8c9d08c38479
Source dataset: uspto-grants-2006_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07151118B2

Reaction notes

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