1H-Pyrrole-2-carboxylic acid, 5-methyl-, ethyl ester → HCID 57435126, compound

HRID 1366951Notes

Reaction equation

HRID 1366951 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:19]=[CH:18][C:17]([CH2:20][C:21](Cl)=[O:22])=[CH:16][CH:15]=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:17]2[CH:16]=[CH:15][C:14]([C:13]([F:24])([F:12])[F:25])=[CH:19][CH:18]=2)[CH:10]=1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 965981H-Pyrrole-2-carboxylic acid, 5-methyl-, ethyl esterHCID 148109432-(4-(Trifluoromethyl)phenyl)acetyl chloride

Product 1

HCID 57435126HCID 57435126, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

5-Methyl-4-[2-(4-trifluoromethyl-phenyl)-acetyl]-1H-pyrrole-2-carboxylic acid ethyl ester (117) was synthesized from 5-methyl-1H-pyrrole-2-carboxylic acid ethyl ester (107) and (4-trifluoromethylphenyl)-acetyl chloride following the procedure described in Example 32. Reaction Conditions: 1,2-dichloroethane/−40° C. Purification: prep/HPLC. Yield: 33%. 1H (CDCl3, 400 MHz): δ 10.5 (NH, broad s), 7.56 (2H, d), 7.34 (2H, d), 7.32 (1H, s), 4.37 (2H, q), 4.15 (2H, s), 2.59 (3H, s), 1.38 (3H, t) ppm. 13C (CDCl3, 100 MHz): δ 193.3, 161.5, 141.0, 139.0, 130.9, 125.5, 128.6, 121.4, 120.6, 114.0 61.0, 46.5, 14.5, 14.0 ppm. LC/MS: 98%.

Workup

  1. customReaction Conditions
  2. customPurification

Sources & evidence

ORD record
ord-93990fcd355b4081a77f6f90e3c4b970
Source dataset
uspto-grants-2011_02
Patent number
US07893098B2

Reaction notes

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