Methyl iodide → HCID 12790366, compound

HRID 1577632Notes

Reaction equation

HRID 1577632 reaction equation
[H-].[Na+].[O:3]1[C:14]2[C:13]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[NH:7][C:6]=2[CH:5]=[C:4]1[C:15]([O:17][CH2:18][CH3:19])=[O:16].[CH3:20]I>CN(C)C=O>[CH3:20][N:7]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:13]=2[C:14]2[O:3][C:4]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:5][C:6]1=2

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 12521832HCID 12521832, compound

Product 1

HCID 12790366HCID 12790366, compoundYield 84.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of sodium hydride (2.5 g) in dimethylformamide (100 ml), a solution of ethyl furo[3,2-b]indole-2-carboxylate (20 g) in dimethylformamide (100 ml) was added dropwise with stirring, then the mixture was stirred for 0.5 hour at room temperature. Methyl iodide (30 g) was added, and the resulting mixture was stirred for 5 hours at room temperature to give ethyl 4-methyl-furo[3,2-b]indole-2-carboxylate (18 g), which was hydrolyzed in a solution of sodium hydroxide (20 g) in water (200 ml) with stirring for an hour to give 4-methyl-furo[3,2-b]indole-2-carboxylic acid (15 g). This carboxylic acid was treated with thionyl chloride (50 ml) in benzene (70 ml) with stirring for an hour at 50° C. to give 4-methyl-furo[3,2-b]indole-2-carbonyl chloride (12 g).

Workup

  1. stirringthe mixture was stirred for 0.5 hour at room temperature
  2. stirringthe resulting mixture was stirred for 5 hours at room temperature

Sources & evidence

ORD record
ord-72edc3dcf19d485c8f189b925dec4ac4
Source dataset
uspto-grants-1981_09
Patent number
US04288596

Reaction notes

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