Methyl iodide → HCID 66723602, compound

HRID 928448Notes

Reaction equation

HRID 928448 reaction equation
[CH3:1][C:2]1[NH:3][C:4]2[C:9]([CH:10]=1)=[CH:8][C:7]([C:11]([O:13][CH3:14])=[O:12])=[CH:6][CH:5]=2.[CH2:15]1COCC1.IC>>[CH3:15][N:3]1[C:4]2[C:9](=[CH:8][C:7]([C:11]([O:13][CH3:14])=[O:12])=[CH:6][CH:5]=2)[CH:10]=[C:2]1[CH3:1]

Participants

4

Reactant 3

HCID 6328Methyl iodideHCID 8028TetrahydrofuranHCID 12230324HCID 12230324, compound

Product 1

HCID 66723602HCID 66723602, compound

Procedure

To a solution of Methyl 2-methyl-1H-indole-5-carboxylate (1000 mg, 5.29 mmol) in THF (53 ml) KOtBu (723 mg, 6.44 mmol) was added and subsequently Iodomethane (1.05 ml, 16.81 mmol) was added at rt. The reaction mixture was stirred at it for 40 hours. The orange reaction mixture was quenched with water/brine and extracted twice with EA. The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated under vacuum to afford crude methyl 1,2-Dimethyl-1H-indole-5-carboxylate.

Workup

  1. customThe orange reaction mixture was quenched with water/brine
  2. extractionextracted twice with EA
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-cc2de3f3ad1a4cae9e0eb777ed33a63a
Source dataset
uspto-grants-2016_03
Patent number
US09290485B2

Reaction notes

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