Methyl iodide → 6-Bromo-1-methyl-1H-pyrrolo[3,2-b]pyridine

HRID 75272Notes

Reaction equation

HRID 75272 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:5]=[C:6]2[NH:12][CH:11]=[CH:10][C:7]2=[N:8][CH:9]=1.I[CH3:14]>CN(C=O)C.CCOC(C)=O>[Br:3][C:4]1[CH:5]=[C:6]2[N:12]([CH3:14])[CH:11]=[CH:10][C:7]2=[N:8][CH:9]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 242292566-Bromo-1H-pyrrolo[3,2-b]pyridine

Product 1

HCID 673831026-Bromo-1-methyl-1H-pyrrolo[3,2-b]pyridineYield 93%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Sodium hydride (60%, 670 mg, 16.8 mmol) was added to a solution of 6-bromo-1H-pyrrolo[3,2-b]pyridine (3.00 g, 15.2 mmol) in DMF (20 mL) at 0° C., and the reaction mixture was stirred for 30 minutes. Iodomethane (1.05 mL, 16.8 mmol) was added. The reaction mixture was subsequently stirred for 30 minutes while warming to RT, diluted with EtOAc, quenched and washed with brine. The aqueous layer was extracted with EtOAc (2×) and the combined organic layers were dried over MgSO4, concentrated, and purified by silica gel chromatography (50% EtOAc/DCM) to give the title compound as a white solid (2.98 g, 93%). 1H NMR (500 MHz, DMSO-d6) δ ppm 8.38 (d, 1H, J=2.0 Hz), 8.21 (d, 1H, J=2.0 Hz), 7.65 (d, 1H, J=3.5 Hz), 6.57 (d, 1H, J=3.5 Hz), 3.81 (s, 3H); ESI-MS m/z [M+H]+ calc'd for C8H7BrN2, 211, 213; found 211, 213.

Workup

  1. stirringThe reaction mixture was subsequently stirred for 30 minutes
  2. customquenched
  3. washwashed with brine
  4. extractionThe aqueous layer was extracted with EtOAc (2×)
  5. dry with materialthe combined organic layers were dried over MgSO4
  6. concentrationconcentrated
  7. custompurified by silica gel chromatography (50% EtOAc/DCM)

Sources & evidence

ORD record
ord-7b662015993e4db0b119213dd6a5835a
Source dataset
uspto-grants-2014_09
Patent number
US08835420B2

Reaction notes

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