Water → HCID 12459981, compound

HRID 1469664Notes

Reaction equation

HRID 1469664 reaction equation
[CH2:1]([O:8][C:9]([C:11]1[NH:12][C:13]([CH:16]=[O:17])=[CH:14][CH:15]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:18](=O)([O-])[O-].[Cs+].[Cs+].CI.O>CN(C=O)C>[CH:16]([C:13]1[N:12]([CH3:18])[C:11]([C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[O:10])=[CH:15][CH:14]=1)=[O:17]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 71349636Benzyl 5-formyl-1H-pyrrole-2-carboxylate

Product 1

HCID 12459981HCID 12459981, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 5-formyl-1H-pyrrole-2-carboxylic acid benzyl ester (from the preparation of Intermediate 18) (400 mg, 1.75 mmol) in DMF (10 mL) is added cesium carbonate (853 mg, 2.62 mmol) and MeI (297 mg, 2.09 mmol). The mixture is stirred at room temperature for 2 hours then water is added and the mixture is extracted with ethyl acetate (3×). The combined organic layers are washed with water and brine then is dried over magnesium sulfate. The solvent is removed under reduced pressure to give benzyl 5-formyl-1-methyl-1H-pyrrole-2-carboxylate; HPLC Retention time 1.26 minutes (condition C): MS 244.3 (M+1).

Workup

  1. extractionthe mixture is extracted with ethyl acetate (3×)
  2. washThe combined organic layers are washed with water and brine
  3. dry with materialthen is dried over magnesium sulfate
  4. customThe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-22911bb75dd14b2ead056d5b60a33a65
Source dataset
uspto-grants-2015_04
Patent number
US09006249B2

Reaction notes

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