HCID 76852932, compound → HCID 76851465, compound

HRID 1821913Notes

Reaction equation

HRID 1821913 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[CH:10]=[C:9]([CH2:11][OH:12])[NH:8][C:5]2=[CH:6][N:7]=1>C(Cl)Cl.[O-2].[O-2].[Mn+4]>[Cl:1][C:2]1[CH:3]=[C:4]2[CH:10]=[C:9]([CH:11]=[O:12])[NH:8][C:5]2=[CH:6][N:7]=1

Participants

4

Reactant 1

HCID 76852932HCID 76852932, compound

Product 1

HCID 76851465HCID 76851465, compoundYield 70.2%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

(5-Chloro-1H-pyrrolo[2,3-c]pyridin-2-yl)methanol (225 mg, 1.23 mmol) was dissolved in methylene chloride (25 mL). Manganese dioxide (1.07 g, 12.3 mmol) was added and the reaction mixture was stirred for 4 days. The reaction mixture was filtered through diatomaceous earth and the filter cake was washed several times with hot ethyl acetate. The filtrate was concentrated to give 5-chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxaldehyde (156 mg, 70%) as a tan solid: 1H NMR (300 MHz, Acetone-d6) δ7.43 (1H, s), 7.80 (1H, s), 8.77 (1H, s), 10.08 (1H, s), 11.49 (1H, br s).

Workup

  1. filtrationThe reaction mixture was filtered through diatomaceous earth
  2. washthe filter cake was washed several times with hot ethyl acetate
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-4e1a66326c3143119ce6764b8f362c52
Source dataset
uspto-grants-2009_10
Patent number
US07608627B2

Reaction notes

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