3-Chloro-4-fluoroaniline → 5-bromo-2-[(3-chloro-4-fluoro-phenylamino)-(5-chloro-pyridin-2-yl)-methyl]-1-isopropyl-1H-pyrrole-3-carboxylic acid methyl ester

HRID 2204353Notes

Reaction equation

HRID 2204353 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:9]=[C:8]([Br:10])[N:7]([CH:11]([CH3:13])[CH3:12])[C:6]=1[CH:14]([C:16]1[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][N:17]=1)O)=[O:4].[Cl:23][C:24]1[CH:25]=[C:26]([CH:28]=[CH:29][C:30]=1[F:31])[NH2:27].C(OC(C1C=CN(C(C)C)C=1C(C1C=CC(Cl)=CC=1)O)=O)C.NC1C(=O)N(C)C=C(Cl)C=1>>[CH3:1][O:2][C:3]([C:5]1[CH:9]=[C:8]([Br:10])[N:7]([CH:11]([CH3:13])[CH3:12])[C:6]=1[CH:14]([NH:27][C:26]1[CH:28]=[CH:29][C:30]([F:31])=[C:24]([Cl:23])[CH:25]=1)[C:16]1[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][N:17]=1)=[O:4]

Participants

5

Reactant 4

HCID 97083-Chloro-4-fluoroanilineHCID 867031052-[(4-chloro-phenyl)-hydroxy-methyl]-1-isopropyl-1H-pyrrole-3-carboxylic acid ethyl esterHCID 867031183-Amino-5-chloro-1-methylpyridin-2(1H)-oneHCID 867031615-bromo-2-[(5-chloro-pyridin-2-yl)-hydroxy-methyl]-1-isopropyl-1H-pyrrole-3-carboxylic acid methyl ester

Product 1

HCID 867031605-bromo-2-[(3-chloro-4-fluoro-phenylamino)-(5-chloro-pyridin-2-yl)-methyl]-1-isopropyl-1H-pyrrole-3-carboxylic acid methyl ester

Procedure

The title compound was prepared in analogy to the procedure described for Step L3 but 5-bromo-2-[(5-chloro-pyridin-2-yl)-hydroxy-methyl]-1-isopropyl-1H-pyrrole-3-carboxylic acid methyl ester (Step BK2) and 3-chloro-4-fluoroaniline [367-21-5] were used instead of 2-[(4-chloro-phenyl)-hydroxy-methyl]-1-isopropyl-1H-pyrrole-3-carboxylic acid ethyl ester and 3-amino-5-chloro-1-methyl-1H-pyridin-2-one respectively. The title compound was obtained as a beige foam. ESI-MS: tR=1.51 min, [M+H]+ 514/516/518 (LC-MS 1).

Workup

  1. customThe title compound was prepared in analogy to the procedure

Sources & evidence

ORD record
ord-c6f1cc08bf70474d8417c8d056d9700e
Source dataset
uspto-grants-2016_06
Patent number
US09365576B2

Reaction notes

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