Cesium carbonate → HCID 89826318, compound

HRID 2272950Notes

Reaction equation

HRID 2272950 reaction equation
[CH3:1][O:2][C:3]([C:5]1[NH:6][CH:7]=[CH:8][CH:9]=1)=[O:4].[F:10][C:11]([F:22])([F:21])[C:12]1[CH:17]=[CH:16][C:15]([C:18](=[O:20])[CH3:19])=[CH:14][CH:13]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C>[CH3:1][O:2][C:3]([C:5]1[N:6]([CH2:19][C:18](=[O:20])[C:15]2[CH:14]=[CH:13][C:12]([C:11]([F:10])([F:21])[F:22])=[CH:17][CH:16]=2)[CH:7]=[CH:8][CH:9]=1)=[O:4]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 697311-(4-(Trifluoromethyl)phenyl)ethan-1-oneHCID 136930Methyl pyrrole-2-carboxylate

Product 1

HCID 89826318HCID 89826318, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
35 °C

Procedure

A solution of 1.15 g (9.19 mmol) 1H-pyrrole-2-carboxylic acid methyl ester and 2.70 g (10.1 mmol) 2-bromo-(1-(4-trifluoromethyl-phenyl)-ethanone in 20 ml acetonitrile is treated with 3.30 g (10.1 mmol) cesium carbonate. The resulting suspension is stirred at 35° C. for 18 hours. The reaction mixture is filtered and the filtrate is evaporated. The residue is chromatographed on a silica gel column with cyclohexane/ethyl acetate as eluent to give 1-[2-oxo-2-(4-trifluoromethyl-phenyl)-ethyl]-1H-pyrrole-2-carboxylic acid methyl ester as yellow oil; HPLC/MS 2.52 (A), [M+H] 312.

Workup

  1. filtrationThe reaction mixture is filtered
  2. customthe filtrate is evaporated
  3. customThe residue is chromatographed on a silica gel column with cyclohexane/ethyl acetate as eluent

Sources & evidence

ORD record
ord-4eb205704c8e4cdb8e665e43ce44d207
Source dataset
uspto-grants-2015_09
Patent number
US09120805B2

Reaction notes

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