Methyl iodide → Benzyl 1-methyl-1H-indole-6carboxylate

HRID 322086Notes

Reaction equation

HRID 322086 reaction equation
[H-].[Na+].[NH:3]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]([O:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[O:13])[CH:10]=2)[CH:5]=[CH:4]1.[CH3:22]I>O1CCCC1>[CH3:22][N:3]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]([O:14][CH2:15][C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)=[O:13])[CH:10]=2)[CH:5]=[CH:4]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 22009945benzyl 1H-indole-6-carboxylate

Product 1

HCID 11265573Benzyl 1-methyl-1H-indole-6carboxylateYield 89.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride (1.03 g of a 60% dispersion in paraffin oil) was added portionwise to a stirred solution of benzyl 1H-indole-6-carboxylate (from (a), 5.4 g, 21.5 mmol) in tetrahydrofuran (80 ml) at 0° C. under a nitrogen atmosphere. The mixture was stirred for 2 h, then methyl iodide (2.04 ml, 32.6 mmol) was added dropwise. The solution was allowed to warm to room temperature over 12 h. The reaction was quenched by the slow addition of ice cold water and the tetrahydrofuran was removed in vacuo. The product was extracted from saturated sodium chloride solution (300 ml) with dichloromethane (2×300 ml) and the organics were dried (MgSO4). The dried organics were filtered through a 5 cm plug of silica in a sintered funnel and concentrated in vacuo to give the subtitle compound as a white solid (5.1 g).

Workup

  1. customThe reaction was quenched by the slow addition of ice cold water
  2. customthe tetrahydrofuran was removed in vacuo
  3. extractionThe product was extracted from saturated sodium chloride solution (300 ml) with dichloromethane (2×300 ml)
  4. dry with materialthe organics were dried (MgSO4)
  5. filtrationThe dried organics were filtered through a 5 cm plug of silica in a sintered funnel
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a646d4ec080440f5875e960ee582d046
Source dataset
uspto-grants-2001_04
Patent number
US06211223B1

Reaction notes

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