HCID 71209178, compound → HCID 86675743, compound

HRID 1912600Notes

Reaction equation

HRID 1912600 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:19]=[CH:20][C:21]=1[F:22])[CH2:5][N:6]1[C:10]2=[N:11][C:12]([CH3:18])=[C:13]([CH2:16][OH:17])[C:14]([I:15])=[C:9]2[CH:8]=[CH:7]1.C1C=C[NH+]=CC=1.[O-][Cr](Cl)(=O)=O>C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([CH:19]=[CH:20][C:21]=1[F:22])[CH2:5][N:6]1[C:10]2=[N:11][C:12]([CH3:18])=[C:13]([CH:16]=[O:17])[C:14]([I:15])=[C:9]2[CH:8]=[CH:7]1

Participants

4

Reactant 2

HCID 71209178HCID 71209178, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 86675743HCID 86675743, compoundYield 73.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (1-(3,4-difluorobenzyl)-4-iodo-6-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl)methanol (5.0 g, 8.45 mmol) in DCM (85 mL) at 0° C. was added PCC (3.64 g, 16.90 mmol) and the mixture was stirred at RT for 4 h. The mixture was adsorbed on silica gel and purified by column chromatography to provide 1-(3,4-difluorobenzyl)-4-iodo-6-methyl-1H-pyrrolo[2,3-b]pyridine-5-carbaldehyde (3.0 g, 6.19 mmol, 73.2% yield) as an off-white solid. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 2.91 (s, 3 H), 5.45 (s, 2 H), 6.56 (d, J=3.71 Hz, 1 H), 6.91-7.19 (m, 3 H), 7.22 (d, J=3.51 Hz, 1 H), m10.40 (s, 1H); LCMS (m/z) ES+=413 (M+1).

Workup

  1. custompurified by column chromatography

Sources & evidence

ORD record
ord-cafd4d300be54a16ab40c9e4ad91a371
Source dataset
uspto-grants-2013_12
Patent number
US08609653B2

Reaction notes

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