Sodium hydride → 1H-Pyrrolo(2,3-b)pyridine

HRID 893379Notes

Reaction equation

HRID 893379 reaction equation
C([C:4]1[NH:12][C:7]2=[N:8][CH:9]=[CH:10][CH:11]=[C:6]2[CH:5]=1)CC.[H-].[Na+].C(OC(C1C=CC=CC=1C1C=CC(CBr)=CC=1)=O)(C)(C)C>O>[NH:12]1[C:7]2=[N:8][CH:9]=[CH:10][CH:11]=[C:6]2[CH:5]=[CH:4]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 9906257tert-Butyl 4'-(bromomethyl)biphenyl-2-carboxylateHCID 189467102-Propyl-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 92221H-Pyrrolo(2,3-b)pyridine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 2-propyl-1H-pyrrolo[2,3-b]-pyridine prepared in Example 1 step 3 (0.1M in DMF) is added NaH (1.1 equivalent of an 80% dispersion in oil, 0.271 mmol). After 20 min, 2-t-butoxycarbonyl-4'-bromomethylbiphenyl (1.1 equivalent) is added and the mixture is stirred for 30 min. Water is added and the mixture extracted with EtOAc. Purification by flash chromatography (SiO2, 25% EtOAc/hexanes) gives 2-propyl-1-[(2'-t-butoxycarbonyl)-[1,1']-biphenyl-4-yl)methyl]-1H-pyrrolo[2,3-b]pyridine.

Workup

  1. extractionthe mixture extracted with EtOAc
  2. customPurification by flash chromatography (SiO2, 25% EtOAc/hexanes)

Sources & evidence

ORD record
ord-55d69e611b8344dabbc8a1db74984c2a
Source dataset
uspto-grants-1992_06
Patent number
US05124335

Reaction notes

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