(1-(2,3-difluorobenzyl)-4-iodo-6-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl)methanol → 1-(2,3-difluorobenzyl)-4-iodo-6-methyl-1H-pyrrolo[2,3-b]pyridine-5-carbaldehyde

HRID 1912616Notes

Reaction equation

HRID 1912616 reaction equation
[F:1][C:2]1[C:21]([F:22])=[CH:20][CH:19]=[CH:18][C:3]=1[CH2:4][N:5]1[C:9]2=[N:10][C:11]([CH3:17])=[C:12]([CH2:15][OH:16])[C:13]([I:14])=[C:8]2[CH:7]=[CH:6]1.C1C=C[NH+]=CC=1.[O-][Cr](Cl)(=O)=O>ClCCl>[F:1][C:2]1[C:21]([F:22])=[CH:20][CH:19]=[CH:18][C:3]=1[CH2:4][N:5]1[C:9]2=[N:10][C:11]([CH3:17])=[C:12]([CH:15]=[O:16])[C:13]([I:14])=[C:8]2[CH:7]=[CH:6]1

Participants

4

Reactant 2

HCID 71209443(1-(2,3-difluorobenzyl)-4-iodo-6-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl)methanolHCID 178418287HCID 178418287, compound2×

Product 1

HCID 866757441-(2,3-difluorobenzyl)-4-iodo-6-methyl-1H-pyrrolo[2,3-b]pyridine-5-carbaldehydeYield 94.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (1-(2,3-difluorobenzyl)-4-iodo-6-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl)methanol (8.75 g, 21.13 mmol) in dichloromethane (DCM) (200 mL) at 0° C. was added PCC (9.11 g, 42.3 mmol) and silica gel (6.4 g, 70% wt. of the amount of PCC) and the mixture was stirred at ambient temperature for 3 h. The mixture was filtered through silica gel washing with dichloromethane (1 L). The filtrate was concentrated to provide 1-(2,3-difluorobenzyl)-4-iodo-6-methyl-1H-pyrrolo[2,3-b]pyridine-5-carbaldehyde (9.44 g, 19.93 mmol, 94% yield) as a brownish solid. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 2.90 (s, 3H), 5.56 (s, 2 H), 6.54 (d, J=3.71 Hz, 1 H), 6.88-7.05 (m, 2 H), 7.05-7.19 (m, 1 H), 7.30 (d, J=3.51 Hz, 1 H), 10.38 (s, 1 H); LCMS (m/z) ES+=412 (M+1).

Workup

  1. filtrationThe mixture was filtered through silica gel washing with dichloromethane (1 L)
  2. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-33f6332600e44bf1a018f7c5817f73ae
Source dataset
uspto-grants-2013_12
Patent number
US08609653B2

Reaction notes

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