1H-Pyrrole-2-carboxylic acid, 5-methyl-, ethyl ester → 4-[2-(3-Fluoro-phenyl)-acetyl]-5-methyl-1H-pyrrole-2-carboxylic acid ethyl ester

HRID 1434801Notes

Reaction equation

HRID 1434801 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]([CH3:11])=[CH:9][CH:10]=1)=[O:5])[CH3:2].[F:12][C:13]1[CH:14]=[C:15]([CH2:19][C:20](Cl)=[O:21])[CH:16]=[CH:17][CH:18]=1>ClCCCl>[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]([CH3:11])=[C:9]([C:20](=[O:21])[CH2:19][C:15]2[CH:16]=[CH:17][CH:18]=[C:13]([F:12])[CH:14]=2)[CH:10]=1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 965981H-Pyrrole-2-carboxylic acid, 5-methyl-, ethyl esterHCID 127516352-(3-Fluorophenyl)acetyl chloride

Product 1

HCID 574351244-[2-(3-Fluoro-phenyl)-acetyl]-5-methyl-1H-pyrrole-2-carboxylic acid ethyl esterYield 78%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

4-[2-(3-Fluorophenyl)-acetyl]-5-methyl-1H-pyrrole-2-carboxylic acid ethyl ester (114) was synthesized from 5-methyl-1H-pyrrole-2-carboxylic acid ethyl ester (107) and (3-fluorophenyl)-acetyl chloride following the procedure described in Example 32. Reaction Conditions: 1,2-dichloroethane/RT. Purification: recrystallization from ether/pentane. Yield: 78%. 1H (CDCl3, 400 MHz): δ 10.6 (NH, broad s), 7.30 (1H, s), 7.26 (1H, dd), 7.04 (1H, d), 6.99 (1H, d), 6.92 (1H, dd), 4.37 (2H, q), 4.07 (2H, s), 2.58 (3H, s), 1.39 (3H, t) ppm. 13C (CDCl3, 100 MHz): δ 193.5, 164.0, 161.6, 141.0, 137.4, 130.0, 125.3, 121.5, 120.5, 116.9, 116.4, 113.7, 61.0, 46.4, 14.4, 14.0 ppm. LC/MS: 98%.

Workup

  1. customReaction Conditions
  2. customPurification
  3. customrecrystallization from ether/pentane

Sources & evidence

ORD record
ord-19914b71eadd4a55a30d64da244dbdcd
Source dataset
uspto-grants-2009_11
Patent number
US07615572B2

Reaction notes

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