Dichloromethane → methyl 4-(2,4,6-trifluorobenzoyl)-1H-pyrrole-2-carboxylate

HRID 1894710Notes

Reaction equation

HRID 1894710 reaction equation
ClCCl.[F:4][C:5]1[CH:20]=[C:19]([F:21])[CH:18]=[C:17]([F:22])[C:6]=1[C:7]([C:9]1[CH:10]=[C:11]([C:14]([OH:16])=[O:15])[NH:12][CH:13]=1)=[O:8].[N+](=[CH2:25])=[N-]>C(OCC)C>[F:4][C:5]1[CH:20]=[C:19]([F:21])[CH:18]=[C:17]([F:22])[C:6]=1[C:7]([C:9]1[CH:10]=[C:11]([C:14]([O:16][CH3:25])=[O:15])[NH:12][CH:13]=1)=[O:8]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 9550DiazomethaneHCID 534025784-(2,4,6-Trifluorobenzoyl)-1H-pyrrole-2-carboxylic acid2×

Product 1

HCID 66646907methyl 4-(2,4,6-trifluorobenzoyl)-1H-pyrrole-2-carboxylate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a dichloromethane 70 mL suspension of 4-(2,4,6-trifluorobenzoyl)-1H-pyrrole-2-carboxylic acid (Intermediate 1) (3 g, 11.2 mmol) was added diazomethane solution in diethyl ether upon cooling in an ice-water bath. After stirring for 3 hr, the reaction mixture was concentrated and chromatographed on silica gel eluting with a gradient solvent mixture of AcOEt and hexanes to give the title compound (2.74 g).

Workup

  1. temperatureupon cooling in an ice-water bath
  2. concentrationthe reaction mixture was concentrated
  3. customchromatographed on silica gel eluting with a gradient solvent mixture of AcOEt and hexanes

Sources & evidence

ORD record
ord-7a69ffbf10b94918be2185aeb670408d
Source dataset
uspto-grants-2013_08
Patent number
US08513289B2

Reaction notes

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