Methyl iodide → 7-Fluoro-1-methylindole-3-carboxaldehyde

HRID 1494431Notes

Reaction equation

HRID 1494431 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[NH:9][CH:8]=[C:7]2[CH:11]=[O:12].[H-].[Na+].[CH3:15]I>C1COCC1.[Cl-].[Na+].O>[F:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[N:9]([CH3:15])[CH:8]=[C:7]2[CH:11]=[O:12]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 221391207-Fluoro-1H-indole-3-carbaldehyde

Product 1

HCID 221390377-Fluoro-1-methylindole-3-carboxaldehyde

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 57417360Sodium chloride; waterSolvent

Procedure

7-Fluoroindole-3-carboxaldehyde (2.5 g) in dry THF (20 ml) was added to a cold (0°) suspension of sodium hydride (73.2% dispersion in oil; 652 mg) in dry THF (20 ml) under nitrogen and the mixture was stirred for 1h. Methyl iodide (2.5 ml) was added, and the resulting mixture was stirred for 2h at 0°. The mixture was then poured into saturated brine solution (300 ml) and extracted with ether (2×300 ml). The combined, dried organic extracts were evaporated in vacuo to give the title compound (2.66 g), m.p. 92°-94°.

Workup

  1. extractionextracted with ether (2×300 ml)
  2. customdried organic extracts were evaporated in vacuo

Sources & evidence

ORD record
ord-0e0d425e49294787965c9e099f217849
Source dataset
uspto-grants-1991_06
Patent number
US05026722

Reaction notes

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