(4-(cyclohexylamino)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)methanol → 4-(cyclohexylamino)-1-tosyl-1H-pyrrolo[2,3-b]pyridine-5-carbaldehyde

HRID 1969861Notes

Reaction equation

HRID 1969861 reaction equation
[CH:1]1([NH:7][C:8]2[C:13]([CH2:14][OH:15])=[CH:12][N:11]=[C:10]3[N:16]([S:19]([C:22]4[CH:28]=[CH:27][C:25]([CH3:26])=[CH:24][CH:23]=4)(=[O:21])=[O:20])[CH:17]=[CH:18][C:9]=23)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1>C(Cl)(Cl)Cl.[O-2].[O-2].[Mn+4]>[CH:1]1([NH:7][C:8]2[C:13]([CH:14]=[O:15])=[CH:12][N:11]=[C:10]3[N:16]([S:19]([C:22]4[CH:23]=[CH:24][C:25]([CH3:26])=[CH:27][CH:28]=4)(=[O:21])=[O:20])[CH:17]=[CH:18][C:9]=23)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

4

Reactant 1

HCID 58557792(4-(cyclohexylamino)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)methanol

Product 1

HCID 585572344-(cyclohexylamino)-1-tosyl-1H-pyrrolo[2,3-b]pyridine-5-carbaldehydeYield 87.6%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6212ChloroformSolvent2×

Procedure

A mixture of (4-(cyclohexylamino)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)methanol (1.12 g, 2.80 mmol) and manganese dioxide (5.48 g, 63.1 mmol) in chloroform (70 mL) was stirred at ambient temperature for about 18 h. The reaction mixture was diluted with chloroform (100 mL) and the reaction mixture was filtered through a pad of Celite® while washing with chloroform (50 mL). The filtrate was concd under reduced pressure to give 4-(cyclohexylamino)-1-tosyl-1H-pyrrolo[2,3-b]pyridine-5-carbaldehyde (0.975 g, 87%) as an off white solid: LC/MS (Table 1, Method c) Rt=1.70 min; MS m/z: 398 (M+H)+.

Workup

  1. filtrationthe reaction mixture was filtered through a pad of Celite®
  2. washwhile washing with chloroform (50 mL)

Sources & evidence

ORD record
ord-b36280f743634acb8392486322e8a037
Source dataset
uspto-grants-2013_04
Patent number
US08426411B2

Reaction notes

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