Carbon Dioxide → HCID 14391164, compound

HRID 1381559Notes

Reaction equation

HRID 1381559 reaction equation
[C:1](Cl)(Cl)=[O:2].[NH:5]1[CH:9]=[CH:8][CH:7]=[CH:6]1.C(=O)=O.[NH2:13][C:14]1[CH:15]=[C:16]2[C:20](=[CH:21][CH:22]=1)[NH:19][CH:18]=[C:17]2[CH2:23][C:24]#[N:25]>C1COCC1.CO.N1C=CC=CC=1>[C:24]([CH2:23][C:17]1[C:16]2[C:20](=[CH:21][CH:22]=[C:14]([NH:13][C:1]([C:6]3[NH:5][CH:9]=[CH:8][CH:7]=3)=[O:2])[CH:15]=2)[NH:19][CH:18]=1)#[N:25]

Participants

8

Reactant 4

HCID 280Carbon DioxideHCID 6371Phosgene2×HCID 8027PyrroleHCID 12803100HCID 12803100, compound

Product 1

HCID 14391164HCID 14391164, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 1049PyridineSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Phosgene was passed slowly into 50 ml THF until 4.46 g (0.045 mole) had been collected. To this solution was added 3.04 ml (0.844 mole) of pyrrole and the mixture stirred at 5° for 3 hours. The excess phosgene was driven off by heating and trapped in a NaOH trap to monitor CO2 evolution. The reaction mixture was cooled, treated with 10 ml pyridine followed by a solution of 2.0 g (0.012 mole) of 5-aminoindole-3-acetonitrile, Example 1, in 50 ml THF and stirred 18 hours. Methanol was added to effect complete solution and 100 g silica gel added to adsorb desired product. The solvent was removed in vacuo and treated silica gel washed with 1.5 l of EtOAc which was then concentrated in vacuo to give crude product. This was further purified by column chromatography (EtOAc/Hexane (4:1) on silica gel) to give 1.16 g (37%) desired product: m.p. 216°-218°.

Workup

  1. customhad been collected
  2. temperatureby heating
  3. customtrapped in a NaOH trap
  4. temperatureThe reaction mixture was cooled
  5. stirringstirred 18 hours
  6. additionadded

Sources & evidence

ORD record
ord-bfa0c6d3604844cca5030cb1b4be0dce
Source dataset
uspto-grants-1989_02
Patent number
US04803218

Reaction notes

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