6-Bromo-1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde → 6-bromo-3-methyl-1H-pyrrolo[2,3-b]pyridine

HRID 879390Notes

Reaction equation

HRID 879390 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[Br:7][C:8]1[N:13]=[C:12]2[NH:14][CH:15]=[C:16]([CH:17]=O)[C:11]2=[CH:10][CH:9]=1>C1COCC1>[Br:7][C:8]1[N:13]=[C:12]2[NH:14][CH:15]=[C:16]([CH3:17])[C:11]2=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 184006656-Bromo-1H-pyrrolo[2,3-b]pyridine-3-carbaldehydeHCID 21226445Aluminium lithium hydride

Product 1

HCID 580865436-bromo-3-methyl-1H-pyrrolo[2,3-b]pyridine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

LAH (1.0M in THF, 4.45 mL, 4.45 mmol) was added dropwise to refluxing 6-bromo-1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde (1000 mg, 4.45 mmol) in dry THF (16 mL). The mixture was refluxed for 1 h, allowed to attain room temperature, and quenched with water (0.34 mL), w/w 15% aq. NaOH (0.34 mL) and water (1 mL). The resulting precipitation was filtered off, the filtrate concentrated and the residue was partitioned between aqueous NaOH and DCM. The organic layers were combined, dried and concentrated to give title compound. LCMS-ESI+: calc'd for C8H7BrN2: 211.2 (M+H+); Found: 211.2 (M+H+).

Workup

  1. temperatureThe mixture was refluxed for 1 h
  2. customto attain room temperature
  3. customquenched with water (0.34 mL), w/w 15% aq. NaOH (0.34 mL) and water (1 mL)
  4. customThe resulting precipitation
  5. filtrationwas filtered off
  6. concentrationthe filtrate concentrated
  7. customthe residue was partitioned between aqueous NaOH and DCM
  8. customdried
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-87e40ba6e25749b0a484ed8411730d26
Source dataset
uspto-grants-2015_03
Patent number
US08987250B2

Reaction notes

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