Pyridine → Phenyl 1H-pyrrolo[2,3-b]pyridin-5-ylcarbamate

HRID 1666339Notes

Reaction equation

HRID 1666339 reaction equation
[NH:1]1[C:5]2=[N:6][CH:7]=[C:8]([NH2:10])[CH:9]=[C:4]2[CH:3]=[CH:2]1.CC#N.N1C=CC=CC=1.Cl[C:21]([O:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:22]>C1COCC1>[NH:1]1[C:5]2=[N:6][CH:7]=[C:8]([NH:10][C:21](=[O:22])[O:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH:9]=[C:4]2[CH:3]=[CH:2]1

Participants

6

Reactant 4

HCID 1049PyridineHCID 6342AcetonitrileHCID 15891Phenyl chloroformateHCID 117151871H-pyrrolo(2,3-b)pyridin-5-amine

Product 1

HCID 66833838Phenyl 1H-pyrrolo[2,3-b]pyridin-5-ylcarbamateYield 23%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1H-pyrrolo[2,3-b]pyridin-5-ylamine (0.50 g, 3.7 mmol, see Synthesis, 2005, No. 15, 2503-2506) in THF (4 mL) and CH3CN (6 mL) was added pyridine (0.36 mL, 4.4 mmol) followed by phenyl chloroformate (0.49 mL, 3.8 mmol) slowly. The reaction was stirred overnight. The mixture was partitioned between water and EtOAc. The aqueous layer was extracted again with EtOAc. The combined organic layer was dried over sodium sulfate, filtered and concentrated. Purification by chromatography (0-100% EtOAc/hexane) provided the desired product as a white solid (0.213 g, 23%). MS M+1: 254.15.

Workup

  1. customSynthesis, 2005
  2. customThe mixture was partitioned between water and EtOAc
  3. extractionThe aqueous layer was extracted again with EtOAc
  4. dry with materialThe combined organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by chromatography (0-100% EtOAc/hexane)

Sources & evidence

ORD record
ord-5d8d5fb570d441229a3200efebeb7834
Source dataset
uspto-grants-2011_10
Patent number
US08044052B2

Reaction notes

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