Methyl iodide → HCID 12459981, compound

HRID 2384086Notes

Reaction equation

HRID 2384086 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.[CH2:18](OC(C1NC(C(O)=O)=CC=1)=O)C1C=CC=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+].CI>CN(C=O)C.O>[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

7

Reactant 4

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 24786837HCID 24786837, compoundHCID 71349636Benzyl 5-formyl-1H-pyrrole-2-carboxylate

Product 1

HCID 12459981HCID 12459981, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 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-21018da9834e4ca6ba2e9473896b0cc3
Source dataset
uspto-grants-2012_09
Patent number
US08263629B2

Reaction notes

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