Pyridine → 4-(5-Phenyl-benzofuran-2-ylmethoxycarbonylamino)-biphenyl-3-carboxylic acid methyl ester

HRID 1070393Notes

Reaction equation

[NH2:1][C:2]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].N1C=CC=CC=1.[C:24](Cl)(Cl)=[O:25].[C:28]1([C:34]2[CH:35]=[CH:36][C:37]3[O:41][C:40]([CH2:42][OH:43])=[CH:39][C:38]=3[CH:44]=2)[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>C1(C)C=CC=CC=1>[CH3:7][O:6][C:4]([C:3]1[CH:8]=[C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:10]=[CH:11][C:2]=1[NH:1][C:24]([O:43][CH2:42][C:40]1[O:41][C:37]2[CH:36]=[CH:35][C:34]([C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)=[CH:44][C:38]=2[CH:39]=1)=[O:25])=[O:5]

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of methyl 2-amino-5-phenylbenzoate (1.2 g, 5.28 mmol) in toluene (17.5 mL) and pyridine (0.75 mL, 9.24 mmol) was added 20% phosgene in toluene (3.97 mL, 7.65 mmol) under nitrogen. The mixture was heated at 90° C. for 1 h, cooled to 25° C. and filtered. The filtrate was taken to dryness. Toluene (30 mL), (5-phenyl-benzofuran-2-yl)-methanol (1.19 g, 5.28 mmol) and 4-dimethyl-aminopyridine (0.064 g, 0.53 mmol) were added to the residue under a nitrogen atmosphere. The mixture was heated at 50° C. for 24 h, then concentrated to dryness. Purification by chromatography followed by crystallization gave 1.04 g of 4-(5-phenyl-benzofuran-2-ylmethoxycarbonylamino)-biphenyl-3-carboxylic acid methyl ester.

Workup

temperaturecooled to 25° C.
filtrationfiltered
temperatureThe mixture was heated at 50° C. for 24 h
concentrationconcentrated to dryness
customPurification by chromatography
customfollowed by crystallization

Sources & evidence

ORD record: ord-7e9c094a1e424cc19d4a56e25a499c1b
Source dataset: uspto-grants-2005_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06903086B2

Reaction notes

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