Methyl iodide → HCID 19799267, compound

HRID 2081215Notes

Reaction equation

HRID 2081215 reaction equation
[H-].[Na+].[F:3][C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:12]=1[NH:11][C:10]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:9]2.[CH3:18]I>C1COCC1>[F:3][C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:12]=1[N:11]([CH3:18])[C:10]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:9]2

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 10104458Ethyl 7-fluoro-1H-indole-2-carboxylate

Product 1

HCID 19799267HCID 19799267, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of sodium hydride (73.2% dispersion in oil; 962 mg) in dry THF (50 ml) under nitrogen at 0° was added ethyl 7-fluoro-1H-indole-2-carboxylate (5.5 g) in dry THF (50 ml), and the mixture was stirred for 1 h. Methyl iodide (2.16 ml) was added, and the mixture was stirred for 2 h, then at 50° for 3 h. The mixture was quenched with 10% aqueous THF (5 ml), diluted with ether (500 ml), washed with saturated brine solution (2×500 ml), dried and evaporated in vacuo to leave an oil. This was purified by FCC eluting with hexane:ether (20:1) to give the title compound (4.53 g) as a liquid, t.l.c. (hexane:ether, 20:1) Rf 0.37.

Workup

  1. stirringthe mixture was stirred for 2 h
  2. waitat 50° for 3 h
  3. customThe mixture was quenched with 10% aqueous THF (5 ml)
  4. additiondiluted with ether (500 ml)
  5. washwashed with saturated brine solution (2×500 ml)
  6. customdried
  7. customevaporated in vacuo
  8. customto leave an oil
  9. customThis was purified by FCC
  10. washeluting with hexane:ether (20:1)

Sources & evidence

ORD record
ord-ea44c22007aa4b4a9857bcc2b1d7794e
Source dataset
uspto-grants-1993_02
Patent number
US05183820

Reaction notes

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