Benzyl Bromide → 1-benzyl-1H-pyrrolo[3,2-b]pyridine

HRID 273315Notes

Reaction equation

HRID 273315 reaction equation
[NH:1]1[C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[H-].[Na+].[CH2:12](Br)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>CN(C=O)C>[CH2:12]([N:1]1[C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 92264-AzaindoleHCID 24758Sodium hydride

Product 1

HCID 452673141-benzyl-1H-pyrrolo[3,2-b]pyridineYield 61.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A solution of 1H-pyrrolo[3,2-b]pyridine (1.30 g, 9.42 mmol) in DMF (15 ml) was treated with sodium hydride (60% in mineral oil, 434 mg, 11.3 mmol) at r.t. until effervescence ceased. After cooling to 0° C. benzyl bromide (1.68 ml, 14.1 mmol) was added and the reaction warmed at 60° C. overnight. The reaction mixture was partitioned between water and EtOAc (50 ml each) and extracted with EtOAc (50 ml). The combined organics were washed with brine (20 ml), dried (MgSO4), filtered and concentrated in vacuo to give the title compound as a brown oil (1.20 g, 58%). δH (CDCl3) 8.39 (1H, d, J 4.4 Hz), 7.48 (1H, d, J 8.2 Hz), 7.30 (1H, d, J 3.1 Hz), 7.26-7.18 (3H, m), 7.04-6.69 (3H, m), 6.67 (1H, d, J 4.4 Hz), 5.11 (2H, s). LCMS (ES+) RT 1.56 ml 209 (M+H+).

Workup

  1. additionwas added
  2. customThe reaction mixture was partitioned between water and EtOAc (50 ml each)
  3. extractionextracted with EtOAc (50 ml)
  4. washThe combined organics were washed with brine (20 ml)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3f233d2f3cda41a996d3f96e2a2c7045
Source dataset
uspto-grants-2008_11
Patent number
US07456286B2

Reaction notes

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