HCID 19936616, compound → HCID 19936666, compound

HRID 36890Notes

Reaction equation

HRID 36890 reaction equation
[Cu]([C:4]#[N:5])C#N.Br[C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[NH:12][CH:11]=[C:10]2[S:16][CH:17]1[CH2:22][CH2:21][N:20]([CH3:23])[CH2:19][CH2:18]1>CN1CCCC1=O>[CH3:23][N:20]1[CH2:19][CH2:18][CH:17]([S:16][C:10]2[C:9]3[C:13](=[CH:14][CH:15]=[C:7]([C:4]#[N:5])[CH:8]=3)[NH:12][CH:11]=2)[CH2:22][CH2:21]1

Participants

4

Reactant 2

HCID 19936616HCID 19936616, compoundHCID 178418260HCID 178418260, compound

Product 1

HCID 19936666HCID 19936666, compoundYield 5.1%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A suspension of copper cyanide (17.7 g) and 5-bromo-3-[(1-methylpiperidin-4-yl)thio]-1H-indole (35.5 g, prepared in Example 44) in 1-methylpyrrolidin-2-one (45 ml) is refluxed for 24 hours. After dilution with water, the brown precipitate is separated off and then taken up with a mixture of water (110 ml) and ethylenediamine (170 ml). The blue solution is extracted with ethyl acetate. The organic phase is dried over sodium sulfate and concentrated. The residual oil is chromatographed on silica gel (eluent: AcOEt/iPrNH2 95/5) to give 3-[(1-methylpiperidin-4-yl)thio]-1H-indole-5-carbonitrile (1.5 g), which is converted to the oxalate in ethanol.

Workup

  1. temperatureis refluxed for 24 hours
  2. customAfter dilution with water, the brown precipitate is separated off
  3. additiontaken up with a mixture of water (110 ml) and ethylenediamine (170 ml)
  4. extractionThe blue solution is extracted with ethyl acetate
  5. dry with materialThe organic phase is dried over sodium sulfate
  6. concentrationconcentrated
  7. customThe residual oil is chromatographed on silica gel (eluent: AcOEt/iPrNH2 95/5)

Sources & evidence

ORD record
ord-92d1c80f306a46dbbaab62e930a59704
Source dataset
uspto-grants-1995_05
Patent number
US05418242

Reaction notes

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