HCID 11217626, compound → 7-Chloro-1H-pyrrolo[2,3-c]pyridine-2-carbaldehyde

HRID 1821907Notes

Reaction equation

HRID 1821907 reaction equation
[Cl:1][C:2]1[N:3]=[CH:4][CH:5]=[C:6]2[CH:10]=[C:9]([CH2:11][OH:12])[NH:8][C:7]=12>[O-2].[Mn+4].[O-2].ClCCl>[Cl:1][C:2]1[N:3]=[CH:4][CH:5]=[C:6]2[CH:10]=[C:9]([CH:11]=[O:12])[NH:8][C:7]=12

Participants

4

Reactant 1

HCID 11217626HCID 11217626, compound

Product 1

HCID 578935647-Chloro-1H-pyrrolo[2,3-c]pyridine-2-carbaldehydeYield 86.4%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of (7-chloro-1H-pyrrolo[2,3-c]pyridin-2-yl)methanol (Example 1) (2.81 g, 15.4 mmol), manganese(IV)oxide (16 g) and dichloromethane (250 mL) was stirred under an atmosphere of nitrogen for 16 h. The mixture was filtered through a pad of diatomaceous earth, washing generously with hot acetone. Evaporation of the solvents provided 7-chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxaldehyde (2.40 g, 13.3 mmol, 84%) as a mixture of aldehyde and aldehyde hydrate: 1H NMR (300 MHz, CD3OD) δ5.79 (1H, s), 6.65 (1H, s), 7.44 (1H, s), 7.53 (1H, d, J=5.5 Hz), 7.72 (1H, d, J=5.5 Hz), 7.85 (1H, d, J=5.5 Hz), 7.99 (1H, d, J=5.5 Hz), 10.02 (1H, s); ESI MS m/z 181 [C8H5ClN2O+H]+.

Workup

  1. filtrationThe mixture was filtered through a pad of diatomaceous earth
  2. washwashing generously with hot acetone
  3. customEvaporation of the solvents

Sources & evidence

ORD record
ord-822f00288f664837995491054ad02b8e
Source dataset
uspto-grants-2009_10
Patent number
US07608627B2

Reaction notes

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