Ethyl diazoacetate → 5-(3-Fluoro-2'-methanesulfonyl-biphenyl-4-ylcarbamoyl)-4,5-dihydro-1H-pyrazole-3-carboxylic acid ethyl ester

HRID 1796317Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[S:19]([CH3:22])(=[O:21])=[O:20])[CH:5]=[CH:6][C:7]=1[NH:8][C:9](=[O:12])[CH:10]=[CH2:11].[N+:23](=[CH:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])=[N-:24]>C(OCC)(=O)C>[CH2:29]([O:28][C:26]([C:25]1[CH2:11][CH:10]([C:9](=[O:12])[NH:8][C:7]2[CH:6]=[CH:5][C:4]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[S:19]([CH3:22])(=[O:21])=[O:20])=[CH:3][C:2]=2[F:1])[NH:24][N:23]=1)=[O:27])[CH3:30]

Participants

Conditions

Temperature: 60 °C

Procedure

To N-(3-Fluoro-2′-methanesulfonyl-biphenyl-4-yl)-acrylamide (4.47 g) in ethyl acetate (150 ml) was added ethyl diazoacetate (1.5 equiv.) and the mixture heated at 60° C. for 24 hours. Evaporated and then columned: eluant 10-100 EtOAc in hexane. Collected 5-(3-fluoro-2′-methanesulfonyl-biphenyl-4-ylcarbamoyl)-4,5-dihydro-1H-pyrazole-3-carboxylic acid ethyl ester (1.67 g)

Workup

customEvaporated

Sources & evidence

ORD record: ord-9295ef98236c4f2b8535f4c1c9997c38
Source dataset: uspto-grants-2006_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07030141B2

Reaction notes

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