Cesium carbonate → HCID 89826327, compound

HRID 2272948Notes

Reaction equation

HRID 2272948 reaction equation
[CH3:1][O:2][C:3]([C:5]1[NH:6][CH:7]=[CH:8][CH:9]=1)=[O:4].C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:16]([O:23][C:24]1[CH:29]=[CH:28][C:27]([C:30](=[O:33])[CH2:31]Br)=[CH:26][CH:25]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CN(C=O)C>[CH3:1][O:2][C:3]([C:5]1[N:6]([CH2:31][C:30]([C:27]2[CH:28]=[CH:29][C:24]([O:23][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[CH:25][CH:26]=2)=[O:33])[CH:7]=[CH:8][CH:9]=1)=[O:4]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 136930Methyl pyrrole-2-carboxylateHCID 105425931-[4-(Benzyloxy)phenyl]-2-bromoethan-1-one

Product 1

HCID 89826327HCID 89826327, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
50 °C

Procedure

A suspension of 200 mg (1.60 mmol) 1H-pyrrole-2-carboxylic acid methyl ester and 1.56 g (4.79 mmol) cesium carbonate in 3 ml DMF is heated to 50° C. under stirring. Then a solution of 488 mg (1.60 mmol) 1-(4-benzyloxy-phenyl)-2-bromo-ethanone in 1 ml DMF is added within 3 minutes. The reaction mixture is stirred for 18 hours at 50° C. The reaction mixture is filtered with suction and the filtrate is evaporated. The residue is crystallized from diethyl ether to give 1-[2-(4-benzyloxy-phenyl)-2-oxo-ethyl]-1H-pyrrole-2-carboxylic acid methyl ester as beige crystals; HPLC/MS 2.51 min (A), [M+H] 350.

Workup

  1. stirringThe reaction mixture is stirred for 18 hours at 50° C
  2. filtrationThe reaction mixture is filtered with suction
  3. customthe filtrate is evaporated
  4. customThe residue is crystallized from diethyl ether

Sources & evidence

ORD record
ord-5e30b1d97a8a4f63b58b075430946f8d
Source dataset
uspto-grants-2015_09
Patent number
US09120805B2

Reaction notes

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