3-Chloro-2-fluoroaniline → methyl 5-bromo-2-(((3-chloro-2-fluorophenyl)amino)(5-chloropyridin-2-yl)methyl)-1-isopropyl-1H-pyrrole-3-carboxylate

HRID 2204358Notes

Reaction equation

HRID 2204358 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[C:25]([F:31])=[C:26]([CH:28]=[CH:29][CH:30]=1)[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>>[Br:10][C:8]1[N:7]([CH:11]([CH3:13])[CH3:12])[C:6]([CH:14]([NH:27][C:26]2[CH:28]=[CH:29][CH:30]=[C:24]([Cl:23])[C:25]=2[F:31])[C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][N:17]=2)=[C:5]([C:3]([O:2][CH3:1])=[O:4])[CH:9]=1

Participants

5

Reactant 4

HCID 750143-Chloro-2-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 86703167methyl 5-bromo-2-(((3-chloro-2-fluorophenyl)amino)(5-chloropyridin-2-yl)methyl)-1-isopropyl-1H-pyrrole-3-carboxylate

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-2-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 white foam. ESI-MS: tR=1.59 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-55ca47f0ac0b4cc6b6c41905bf2c91c1
Source dataset
uspto-grants-2016_06
Patent number
US09365576B2

Reaction notes

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