Reaction #1225

Reaction equation

water

sodium hydride

methyl 4-iodo-2-pyrrolecarboxylate

iodomethane

→

methyl N-methyl-4-iodo-2-pyrrolecarboxylate

Solvents

DMF

DMF

Conditions

Workup

1. 1
   workup.STIRRINGthe mixture was stirred at room temperature for two hours
2. 2
   Extractionextracted with ethyl ether
3. 3
   Otherthe organic phase decanted
4. 4
   Dryingdried over magnesium sulfate
5. 5
   Otherevaporated
6. 6
   OtherThe residue obtained
7. 7
   Otherwas purified by chromatography on a silica column
8. 8
   Washeluted with a mixture of dichloromethane and hexane (40/60)
9. 9
   Other4.5 g (65%) of methyl N-methyl-4-iodo-2-pyrrolecarboxylate of melting point 64°-65° C. were recovered

Procedure

780 mg (25.9 mmol) of sodium hydride (80% in oil) and 20 ml of DMF were introduced into a three-necked flask, a solution of 6.5 g (25.9 mmol) of methyl 4-iodo-2-pyrrolecarboxylate in 50 ml of DMF was added dropwise and the mixture was stirred until gaseous emission ceased. 2.1 ml (33.6 mmol) of iodomethane were then added and the mixture was stirred at room temperature for two hours. The reaction medium was poured into water, extracted with ethyl ether, the organic phase decanted, dried over magnesium sulfate and evaporated. The residue obtained was purified by chromatography on a silica column eluted with a mixture of dichloromethane and hexane (40/60). 4.5 g (65%) of methyl N-methyl-4-iodo-2-pyrrolecarboxylate of melting point 64°-65° C. were recovered.

Source