3-Pyrroline → n-{3-Chloro-4-[2-(2,5-dihydro-pyrrol-1-yl)-ethoxy]-phenyl}-2-(2-chloro-4-trifluoromethyl-phenoxy)-acetamide

HRID 898596Notes

Reaction equation

HRID 898596 reaction equation
Br[CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12](=[O:26])[CH2:13][O:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][C:16]=2[Cl:25])=[CH:7][C:6]=1[Cl:27].[NH:28]1[CH2:32][CH:31]=[CH:30][CH2:29]1>CCN(C(C)C)C(C)C>[Cl:27][C:6]1[CH:7]=[C:8]([NH:11][C:12](=[O:26])[CH2:13][O:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][C:16]=2[Cl:25])[CH:9]=[CH:10][C:5]=1[O:4][CH2:3][CH2:2][N:28]1[CH2:32][CH:31]=[CH:30][CH2:29]1

Participants

4

Reactant 2

HCID 660593-PyrrolineHCID 59691643N-[4-(2-bromo-ethoxy)-3-chloro-phenyl]-2-(2-chloro-4-trifluoromethyl-phenoxy)-acetamide

Product 1

HCID 10027901n-{3-Chloro-4-[2-(2,5-dihydro-pyrrol-1-yl)-ethoxy]-phenyl}-2-(2-chloro-4-trifluoromethyl-phenoxy)-acetamide

Reagents, catalysts & solvents 1

HCID 81531DiisopropylethylamineSolvent

Procedure

A solution of 0.145 g (0.300 mmol) of N-[4-(2-bromo-ethoxy)-3-chloro-phenyl]-2-(2-chloro-4-trifluoromethyl-phenoxy)-acetamide (Z28b) and 30.6 μL (0.400 mmol) 2,5-dihydro-1H-pyrrole in 2 mL Hünig base was stirred for 3h at 80° C. and then evaporated down i. vac. Column chromatography (Alox, neutral, act. II-III, gradient dichloromethane/MeOH 20:0→19:1) yielded the product.

Workup

  1. customevaporated down i
  2. customColumn chromatography (Alox, neutral, act. II-III, gradient dichloromethane/MeOH 20:0→19:1) yielded the product

Sources & evidence

ORD record
ord-84488ddf730f4c9a9a10261eeca3f45c
Source dataset
uspto-grants-2008_04
Patent number
US07351719B2

Reaction notes

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