Pyridine → 4-(Biphenyl-4-ylmethoxycarbonylamino)-biphenyl-3-carboxylic acid methyl ester

HRID 1070411Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:17])[C:4]1[CH:9]=[C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:7]=[CH:6][C:5]=1[NH2:16].N1C=CC=CC=1.[C:24](Cl)(Cl)=[O:25].[C:28]1([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[CH:33]=[CH:32][C:31]([CH2:34][OH:35])=[CH:30][CH:29]=1>C1(C)C=CC=CC=1.CN(C1C=CN=CC=1)C>[CH3:1][O:2][C:3]([C:4]1[CH:9]=[C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:7]=[CH:6][C:5]=1[NH:16][C:24]([O:35][CH2:34][C:31]1[CH:30]=[CH:29][C:28]([C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=2)=[CH:33][CH:32]=1)=[O:25])=[O:17]

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of methyl-5-phenyl-2-aminobenzoate (0.40 g, 1.76 mmol) and pyridine (0.285 mL, 3.52 mmol) in toluene (7 mL) at room temperature under argon was added 20% phosgene in toluene (1.32 mL, 2.55 mmol) and the mixture was heated at 90° C. for 1 h. The mixture was filtered, and the filtrate was concentrated to dryness. The crude material was dissolved in toluene (10 mL), biphenyl-4-methanol (0.270 g, 1.46 mmol) and DMAP (0.018 g, 0.146 mmol) were added and the mixture was heated at 90° C. for 18 h. The solvent was evaporated to dryness to give 0.51 g of 4-(biphenyl-4-ylmethoxycarbonylamino)-biphenyl-3-carboxylic acid methyl ester.

Workup

filtrationThe mixture was filtered
concentrationthe filtrate was concentrated to dryness
dissolutionThe crude material was dissolved in toluene (10 mL)
temperaturethe mixture was heated at 90° C. for 18 h
customThe solvent was evaporated to dryness

Sources & evidence

ORD record: ord-fe88d1ad620a40e2a04a16d10d0d96d6
Source dataset: uspto-grants-2005_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06903086B2

Reaction notes

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