Methyl iodide → HCID 22485710, compound

HRID 2181176Notes

Reaction equation

HRID 2181176 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:12]=[C:11]2[C:7]([C:8]([CH2:13][C:14]([OH:16])=[O:15])=[CH:9][NH:10]2)=[CH:6][CH:5]=1.I[CH3:18]>C1COCC1>[Cl:3][C:4]1[CH:12]=[C:11]2[C:7]([C:8]([CH2:13][C:14]([OH:16])=[O:15])=[CH:9][N:10]2[CH3:18])=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 3258102-(6-chloro-1H-indol-3-yl)acetic acid

Product 1

HCID 22485710HCID 22485710, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Sodium hydride (0.19 g of 60% suspension in oil) was suspended in dry THF (10 ml). 6-Chloroindole-3-acetic acid (SR058)(100 mg, 0.48 mmol) in THF (5 ml) was added dropwise and the mixture then stirred for 10 minutes. Iodomethane (0.34 g, 2.4 mmol) was then added, and the mixture stirred overnight. Excess sodium hydride was carefully destroyed by dropwise addition of water, and then the mixture was acidified (1M HCl) and extracted with ethyl acetate (3×50 ml), the organic layers dried over MgSO4, and the solvent evaporated to give a brown powder, yield 75 mg, 70%, m.p. 130-132° C. dec.; m/z 225, 223 (M+), 180, 178 (M+-CO2H); δH/ppm 7.46-6.92 (4H, m, Ar—H), 3.77 (3H, s, N—Me), 3.70 (2H, s, ArCH2).

Workup

  1. stirringthe mixture stirred overnight
  2. customExcess sodium hydride was carefully destroyed by dropwise addition of water
  3. extractionextracted with ethyl acetate (3×50 ml)
  4. dry with materialthe organic layers dried over MgSO4
  5. customthe solvent evaporated
  6. customto give a brown powder, yield 75 mg, 70%, m.p. 130-132° C. dec.

Sources & evidence

ORD record
ord-0a2454eadce243aebaa5c8c7bf904cbe
Source dataset
uspto-grants-2005_05
Patent number
US06890948B1

Reaction notes

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