Iodoethane → 2-[N-(Benzyloxycarbonyl)-N-methylaminomethyl]-1-ethyl-1H-indole

HRID 1710521Notes

Reaction equation

HRID 1710521 reaction equation
[H-].[Na+].[CH2:3]([O:10][C:11]([N:13]([CH2:15][C:16]1[NH:17][C:18]2[C:23]([CH:24]=1)=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH3:14])=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH2:25](I)[CH3:26]>CN(C=O)C.O>[CH2:3]([O:10][C:11]([N:13]([CH2:15][C:16]1[N:17]([CH2:25][CH3:26])[C:18]2[C:23]([CH:24]=1)=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH3:14])=[O:12])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

6

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydride2×HCID 574408432-[N-(Benzyloxycarbonyl)-N-methylaminomethyl]-1H-indole

Product 1

HCID 225937652-[N-(Benzyloxycarbonyl)-N-methylaminomethyl]-1-ethyl-1H-indoleYield 87%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

NaH (60% dispersion in mineral oil, 0.25 g, 7.1 mmole) was added portionwise, allowing for gas evolution, to a solution of 2-[N-(benzyloxycarbonyl)-N-methylaminomethyl]-1H-indole (1.40 g, 4.75 mmole) in DMF (35 mL) at 0° C. When the NaH addition was complete, ethyl iodide (0.42 mL, 5.2 mmole) was added at 0° C. The reaction was stirred at 0° C. for 15 minutes then at RT overnight. The reaction was diluted with water and extracted with ethyl acetate. The combined extracts were dried over K2CO3 and concentrated to afford the title compound (1.30 g, 87%) as an orange solid: MS (ES) m/e 323 (M+H)+.

Workup

  1. customat RT
  2. customovernight
  3. extractionextracted with ethyl acetate
  4. dry with materialThe combined extracts were dried over K2CO3
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-266a93fff7c3404787c1679309bc4446
Source dataset
uspto-grants-2010_09
Patent number
US07790716B2

Reaction notes

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