1,8-Diazabicyclo(5.4.0)undec-7-ene → 2-Methyl-5-phenyl-1H-pyrrolo[2,3-c]pyridine

HRID 400605Notes

Reaction equation

HRID 400605 reaction equation
C(OC(=O)[NH:7][C:8]1[CH:9]=[N:10][C:11]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:12][C:13]=1[C:14]#[C:15][CH3:16])(C)(C)C.C1CCN2C(=NCCC2)CC1>CO.O>[CH3:16][C:15]1[NH:7][C:8]2=[CH:9][N:10]=[C:11]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH:12]=[C:13]2[CH:14]=1

Participants

5

Reactant 2

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 60026785(6-Phenyl-4-prop-1-ynylpyridin-3-yl)carbamic acid tert-butyl ester

Product 1

HCID 600266192-Methyl-5-phenyl-1H-pyrrolo[2,3-c]pyridineYield 99.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

A solution of (6-phenyl-4-prop-1-ynylpyridin-3-yl)carbamic acid tert-butyl ester (670 mg, 2.17 mmol) in a mixture of 33 mL of methanol and 11 mL of water was treated with DBU (2.0 mL, 13.4 mmol). The resulting mixture was heated at 60° C. After 24 hours, the mixture was concentrated in vacuo, 50 mL of water was added, the mixture was sonicated, and the resulting solid was filtered. The solid was dried over P2O5 in vacuum to give 450 mg of the title product as a yellow solid (99% yield), which was used without further purification.

Workup

  1. concentrationthe mixture was concentrated in vacuo, 50 mL of water
  2. additionwas added
  3. customthe mixture was sonicated
  4. filtrationthe resulting solid was filtered
  5. dry with materialThe solid was dried over P2O5 in vacuum

Sources & evidence

ORD record
ord-1ad0635c51564572aea0371a72359b89
Source dataset
uspto-grants-2014_06
Patent number
US08741897B2

Reaction notes

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