Water → HCID 58392224, compound

HRID 561371Notes

Reaction equation

HRID 561371 reaction equation
Br[CH2:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:11]=1[N:10]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH:9]=[CH:8]2.[CH3:19][S-:20].[Na+].O>CN(C)C=O>[C:15]([O:14][C:12]([N:10]1[C:11]2[C:7](=[CH:6][CH:5]=[CH:4][C:3]=2[CH2:2][S:20][CH3:19])[CH:8]=[CH:9]1)=[O:13])([CH3:18])([CH3:17])[CH3:16]

Participants

5

Reactant 3

HCID 962WaterHCID 4378561Sodium methanethiolateHCID 21874701tert-Butyl 7-(bromomethyl)-1H-indole-1-carboxylate

Product 1

HCID 58392224HCID 58392224, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

160 mg (516 μmmol) of the compound from Example 6A and 36.2 mg (516 μmol) of sodium methanethiolate were stirred in 5 ml of dimethylformamide at RT for three days. Water was then added, and the mixture was extracted with ethyl acetate. The organic phase was dried over magnesium sulfate, filtered and concentrated. The residue was purified by flash chromatography (mobile phase: cyclohexane/ethyl acetate gradient) to result in 64 mg (45% of theory) of the title compound.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe organic phase was dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by flash chromatography (mobile phase: cyclohexane/ethyl acetate gradient)

Sources & evidence

ORD record
ord-c05c3154dfa5483b9f7922ec019d8c5b
Source dataset
uspto-grants-2011_11
Patent number
US08063234B2

Reaction notes

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