Sodium methanethiolate → HCID 117778949, compound

HRID 2206559Notes

Reaction equation

HRID 2206559 reaction equation
[CH3:1][C:2]1[N:3]([CH:18]([CH:20](OS(C2C=CC(C)=CC=2)(=O)=O)[CH3:21])[CH3:19])[C:4]2[C:9]([C:10]=1[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[CH:8][CH:7]=[CH:6][CH:5]=2.[CH3:33][S-:34].[Na+]>CN(C)C=O>[CH3:1][C:2]1[N:3]([CH:18]([CH:20]([S:34][CH3:33])[CH3:21])[CH3:19])[C:4]2[C:9]([C:10]=1[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[CH:8][CH:7]=[CH:6][CH:5]=2

Participants

4

Reactant 2

HCID 4378561Sodium methanethiolateHCID 89740218HCID 89740218, compound

Product 1

HCID 117778949HCID 117778949, compoundYield 69.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of compound tert-butyl 2-methyl-1-(3-(tosyloxy)butan-2-yl)-1H-indole-3-carboxylate (200 mg, 0.43 mmol) in N,N-dimethyl formamide (2 mL) was added sodium methanethiolate (994 mg, 1.44 mmol). The reaction mixture was stirred at 110° C. for 4 hours. The reaction was quenched by adding water (6 mL). The aqueous layer was extracted with ethyl acetate (30 mL×3), and the organic layer was concentrated. The crude product was purified by preparative TLC (elute: petroleum/ethyl acetate:5:1) to give product tert-butyl 2-methyl-1-(3-(methylthio)butan-2-yl)-1H-indole-3-carboxylate (100 mg, yield: 68%). LRMS (M+H+) m/z: calc'd 333.18. found 334.

Workup

  1. customThe reaction was quenched
  2. additionby adding water (6 mL)
  3. extractionThe aqueous layer was extracted with ethyl acetate (30 mL×3)
  4. concentrationthe organic layer was concentrated
  5. customThe crude product was purified by preparative TLC (elute: petroleum/ethyl acetate:5:1)

Sources & evidence

ORD record
ord-bc13f75304464d6bb294336581d5be01
Source dataset
uspto-grants-2016_06
Patent number
US09371331B2

Reaction notes

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