Sodium hydride → HCID 22007016, compound

HRID 323710Notes

Reaction equation

HRID 323710 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[CH:10][CH:9]=2)=[O:5])[CH3:2].[H-].[Na+].[CH3:17][S:18](Cl)(=[O:20])=[O:19]>C1COCC1>[CH3:17][S:18]([N:7]1[C:8]2[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:14]=[C:6]1[C:4]([O:3][CH2:1][CH3:2])=[O:5])(=[O:20])=[O:19]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 31297Methanesulfonyl chlorideHCID 73125Ethyl indole-2-carboxylate

Product 1

HCID 22007016HCID 22007016, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of ethyl-2-indolecarboxylate (500 mg, 2.64 mmol) in dry THF (5 mL) under an argon atmosphere was cooled to 0° C. and treated with sodium hydride (116 mg, 2.90 mmol). After stirring at room temperature for 5 minutes, the reaction was cooled to 0° C. and treated with methanesulfonyl chloride (0.23 mL, 2.90 mmol). The resulting mixture was gradually warmed to room temperature and stirred for 20 h. The reaction was quenched with saturated NaHCO3 and diluted with ethyl acetate. The organic layer was washed with water and brine, dried over Na2SO4, and concentrated in vacuo. The resulting golden yellow oil was chromatographed over silica gel eluting with 5%, 10%, and 15% ethyl acetate/hexane to provide the title compound (79%, 556.6 mg) as a cream solid. 1H NMR (400 MHz, CDCl3) δ8.05 (d, 1H), 7.65 (d, 1H), 744 (t, 1H), 7.31 (m, 2H), 4.42 (q, 2H), 3.71 (s, 3H), 1.42 (t, 3H).

Workup

  1. temperaturethe reaction was cooled to 0° C.
  2. temperatureThe resulting mixture was gradually warmed to room temperature
  3. stirringstirred for 20 h
  4. customThe reaction was quenched with saturated NaHCO3
  5. additiondiluted with ethyl acetate
  6. washThe organic layer was washed with water and brine
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated in vacuo
  9. customThe resulting golden yellow oil was chromatographed over silica gel eluting with 5%, 10%, and 15% ethyl acetate/hexane

Sources & evidence

ORD record
ord-7934009cea594215880e44e291784ff6
Source dataset
uspto-grants-2001_04
Patent number
US06214856B1

Reaction notes

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