Pyridine → HCID 10221692, compound

HRID 1795864Notes

Reaction equation

HRID 1795864 reaction equation
[C:1]1([S:7][C:8]2[CH:9]=[C:10]3[C:14](=[CH:15][CH:16]=2)[NH:13][C:12]([NH2:17])=[C:11]3[C:18]#[N:19])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.N1C=CC=CC=1.Cl[C:27]([O:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:28]>C1COCC1>[O:29]([C:27]([NH:17][C:12]1[NH:13][C:14]2[C:10]([C:11]=1[C:18]#[N:19])=[CH:9][C:8]([S:7][C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)=[CH:16][CH:15]=2)=[O:28])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 15891Phenyl chloroformateHCID 146332Amphethinile2×

Product 1

HCID 10221692HCID 10221692, compoundYield 49.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 5-phenylsulphanyl-2-amino-1H-indole-3-carbonitrile (0.43 g; 1.62 mmol) [Amphethinile, U.S. Pat. No. 4,533,672] in THF (5 ml) and pyridine (0.17 ml; 2.1 mmol) under argon was cooled to 0° C. and treated dropwise with phenyl chloroformate (0.25 ml; 2.0 mmol). The mixture was allowed to warm to room temperature overnight. After dilution with CH2Cl2 the organic phase was washed with water, then brine and dried over MgSO4. The residue was purified by flash chromatography eluting with increasingly polar mixtures of Et2O/CH2Cl2 (5 to 10% Et2O) to give 2-phenoxycarbonylamino-5-phenylsulphanyl-1H-indole-3-carbonitrile as a beige solid (310 mg).

Workup

  1. washAfter dilution with CH2Cl2 the organic phase was washed with water
  2. dry with materialbrine and dried over MgSO4
  3. customThe residue was purified by flash chromatography
  4. washeluting
  5. temperaturewith increasingly polar mixtures of Et2O/CH2Cl2 (5 to 10% Et2O)

Sources & evidence

ORD record
ord-3b11095e76ec475ca815aa9cf9a4b763
Source dataset
uspto-grants-2006_04
Patent number
US07030123B2

Reaction notes

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