Dimethylformamide → 1H-Pyrrolo[2,3-b]pyridine-3-carboxaldehyde, 1-(methylsulfonyl)-

HRID 489732Notes

Reaction equation

HRID 489732 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][N:8]=2)[CH:3]=[C:2]1C=O.[H-].[Na+].[CH3:14][S:15](Cl)(=[O:17])=[O:16].CN([CH:22]=[O:23])C>C(OCC)(=O)C>[CH3:14][S:15]([N:1]1[C:9]2=[N:8][CH:7]=[CH:6][CH:5]=[C:4]2[C:3]([CH:22]=[O:23])=[CH:2]1)(=[O:17])=[O:16]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 31297Methanesulfonyl chlorideHCID 218736801H-Pyrrolo(2,3-b)pyridine-2-carbaldehyde

Product 1

HCID 222629071H-Pyrrolo[2,3-b]pyridine-3-carboxaldehyde, 1-(methylsulfonyl)-Yield 80%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

7-Azaindole-2-carboxaldehyde (2.31 g, 15.8 mmoles) from step 1 was dissolved in DMF (50 ml). Sodium hydride (0.76 g, 19 mmol) was added and the reaction was stirred at room temperature for 15 min. Methanesulfonyl chloride (1.8 ml, 24 mmoles) was added and the reaction was stirred for 3 h. The reaction mixture was diluted with ethyl acetate and washed trice with 5% lithium chloride solution, then brine. The organic layer was dried (magnesium sulfate) and concentrated to provide 1-methanesulfonyl-1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde (2.84 g, 80% yield). 1H NMR (CDCl3) δ: 3.71 (3H, s), 7.42 (1H, dd, J=4.7 Hz, 8.1 Hz), 8.30 (1H, s), 8.57 (1H, dd, J=1.7 Hz, 4.7 Hz), 8.63 (1H, dd, J=1.7 Hz, 8.1 Hz), 10.07 (s, 1H).

Workup

  1. stirringthe reaction was stirred for 3 h
  2. washwashed trice with 5% lithium chloride solution
  3. dry with materialThe organic layer was dried (magnesium sulfate)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-1807a92e42e842c5ada4949d763fd4d3
Source dataset
uspto-grants-2005_12
Patent number
US06979696B2

Reaction notes

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