Methyl iodide → 1-(5-chloro-1-methyl-1H-indol-2-yl)heptan-1-one

HRID 1818618Notes

Reaction equation

HRID 1818618 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11](=[O:18])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])=[CH:5]2.[H-].[Na+].I[CH3:22]>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH3:22])[C:6]([C:11](=[O:18])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])=[CH:5]2

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 66777278HCID 66777278, compound

Product 1

HCID 667777681-(5-chloro-1-methyl-1H-indol-2-yl)heptan-1-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of the title compound of Example 1 Step B (98.0 mg, 0.37 mmol) in DMF was added NaH (15.0 mg, 60% suspension in mineral oil, 0.37 mmol). After 10 min, iodomethane (0.023 mL, 0.37 mmol) was added, and the mixture was stirred for 2 h, whereupon it was quenched by addition of sat. aq. NaHCO3. The aqueous phase was extracted with EtOAc, and the organic phase was concentrated in vacuo. Purification by flash chromatography on silica gel (0 to 10%, then 10 to 100% EtOAc in hexanes) provided the title compound: LCMS C, tr=2.78 min, m/z 278.3 [M+H]+; 1H NMR (500 MHz, CDCl3) δ 7.65 (app t, J=1.0 Hz, 1H), 7.31 (d, J=1.0 Hz, 2H), 7.20 (s, 1H), 4.05 (s, 3H), 2.95 (t, J=7.0 Hz, 2H), 1.79-1.72 (m, 2H), 1.43-1.26 (m, 6H), 0.90 (t, J=7.5 Hz, 3H).

Workup

  1. customwas quenched by addition of sat. aq. NaHCO3
  2. extractionThe aqueous phase was extracted with EtOAc
  3. concentrationthe organic phase was concentrated in vacuo
  4. customPurification by flash chromatography on silica gel (0 to 10%

Sources & evidence

ORD record
ord-516fbe1fbccd48d7b020e381d331f554
Source dataset
uspto-grants-2009_10
Patent number
US07598398B2

Reaction notes

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