Benzyl Bromide → 1-Benzyl-4-methoxy-2-methyl-1H-pyrrolo[2,3-b]pyridine

HRID 1445923Notes

Reaction equation

HRID 1445923 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]2[NH:11][C:12]([CH3:14])=[CH:13][C:6]=12.[CH2:15](Br)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>CN(C)C(=O)C>[CH2:15]([N:11]1[C:7]2=[N:8][CH:9]=[CH:10][C:5]([O:4][CH3:3])=[C:6]2[CH:13]=[C:12]1[CH3:14])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 117884674-methoxy-2-methyl-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 588959911-Benzyl-4-methoxy-2-methyl-1H-pyrrolo[2,3-b]pyridine

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

To a suspension of sodium hydride (0.292 g, 9.24 mmol) in dry N,N-dimethyl acetamide (10 mL) was added drop-wise under N2, a solution of 4-methoxy-2-methyl-1H-pyrrolo[2,3-b]pyridine 5 (0.60 g, 3.70 mmol) in the same solvent (5 mL). The mixture was stirred at room temperature for 45 min. After this time, the solution was cooled in an ice bath, and benzyl bromide (1.25 g, 7.30 mmol) was slowly added. The solution was allowed to warm at room temperature and stirred for 12 h. Then, it was poured into ice water (30 mL) and stirred for 30 min, and the precipitated solid was extracted with ethylacetate (3×20 mL). The organic layer was washed with water and brine. Concentration and purification on silica gel column using 20% ethylacetate in hexanes gave pure title compound 6 as a white solid. Yield: 0.70 g, 68%; mp 129-131° C.; ESI MS: m/z 253.0 (M+1).

Workup

  1. additionwas added drop-wise under N2
  2. temperatureAfter this time, the solution was cooled in an ice bath
  3. temperatureto warm at room temperature
  4. stirringstirred for 12 h
  5. stirringstirred for 30 min
  6. extractionthe precipitated solid was extracted with ethylacetate (3×20 mL)
  7. washThe organic layer was washed with water and brine
  8. concentrationConcentration and purification on silica gel column

Sources & evidence

ORD record
ord-7958d5dcbe0b4de99b95640d96ecea0c
Source dataset
uspto-grants-2010_02
Patent number
US07666898B2

Reaction notes

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