HCID 68981956, compound → 7-(dibenzylamino)-1H-pyrrolo[2,3-c]pyridine-2-carboxaldehyde

HRID 1821916

Reaction equation

HRID 1821916 reaction equation
[CH2:1]([N:8]([CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:9]1[N:10]=[CH:11][CH:12]=[C:13]2[CH:17]=[C:16]([CH2:18][OH:19])[NH:15][C:14]=12)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C=Cl.[O-2].[O-2].[Mn+4]>[CH2:20]([N:8]([CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:9]1[N:10]=[CH:11][CH:12]=[C:13]2[CH:17]=[C:16]([CH:18]=[O:19])[NH:15][C:14]=12)[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

4

Reactant 1

HCID 68981956HCID 68981956, compound

Product 1

HCID 578935037-(dibenzylamino)-1H-pyrrolo[2,3-c]pyridine-2-carboxaldehydeYield 60%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 5378701Methyl, chloro-Solvent

Procedure

[7-(Dibenzylamino)-1H-pyrrolo[2,3-c]pyridin-2-yl]methanol (3.0 g, 8.74 mmol) was dissolved in methylene chlorine (175 mL). Manganese dioxide (8.0 g, 92 mmol) was added and the reaction mixture was stirred at room temperature for 20 h. The slurry was filtered through diatomaceous earth to remove the catalyst, and the filtrate was concentrated to a dark oil. Purification by Biotage chromatography (10-30% ethyl acetate in hexanes) provided 7-(dibenzylamino)-1H-pyrrolo[2,3-c]pyridine-2-carboxaldehyde (1.78 g, 60%) as a yellow oil: 1H NMR (300 MHz, CDCl3) δ4.89 (4H, s), 7.06-7.12 (2H, m), 7.27-7.38 (10H, m), 7.93 (1H, d, J=5.7 Hz), 8.74 (1H, br s), 9.77 (1H, s).

Workup

  1. filtrationThe slurry was filtered through diatomaceous earth
  2. customto remove the catalyst
  3. concentrationthe filtrate was concentrated to a dark oil
  4. customPurification by Biotage chromatography (10-30% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-c1c4f3fb22ea4648afcab6b4086067e5
Source dataset
uspto-grants-2009_10
Patent number
US07608627B2

Linked notes

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