1H-Pyrrole-2-carboxylic acid, 5-methyl-, ethyl ester → HCID 57435130, compound

HRID 1724804Notes

Reaction equation

HRID 1724804 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]([F:25])([F:24])[C:14]1[CH:15]=[C:16]([CH2:20][C:21](Cl)=[O:22])[CH:17]=[CH:18][CH:19]=1>ClCCCl>[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]([CH3:11])=[C:9]([C:21](=[O:22])[CH2:20][C:16]2[CH:17]=[CH:18][CH:19]=[C:14]([C:13]([F:24])([F:12])[F:25])[CH:15]=2)[CH:10]=1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 965981H-Pyrrole-2-carboxylic acid, 5-methyl-, ethyl esterHCID 127516363-(Trifluoromethyl)phenylacetyl chloride

Product 1

HCID 57435130HCID 57435130, compoundYield 16%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

5-Methyl-4-[2-(3-trifluoromethyl-phenyl)-acetyl]-1H-pyrrole-2-carboxylic acid ethyl ester (120) was synthesized from 5-methyl-1H-pyrrole-2-carboxylic acid ethyl ester (107) and (3-trifluoromethylphenyl)-acetyl chloride following the procedure described in Example 32. Reaction Conditions: 1,2-dichloroethane/−40° C. Purification: prep/HPLC. Yield: 16%. 1H (CDCl3, 400 MHz): δ 10.7 (NH, broad s), 7.48 (4H, m), 7.34 (1H, s), 4.37 (2H, q), 4.15 (2H, s), 2.59 (3H, s), 1.39 (3H, t) ppm. 13C (CDCl3, 100 MHz): δ 193.3, 161.6, 141.2, 136.0, 133.2, 131.2, 128.8, 128.2, 126.4, 123.6, 121.4, 120.6, 116.9, 61.0, 46.3, 14.3, 13.9 ppm. LC/MS: 100%.

Workup

  1. customReaction Conditions
  2. customPurification

Sources & evidence

ORD record
ord-6a1ee48dfae7409fb765f69c7ea43326
Source dataset
uspto-grants-2009_02
Patent number
US07488747B2

Reaction notes

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