Cornforth reagent → 2-(2-(Methylsulfonyl)phenyl)-1,5-naphthyridine-3-carbaldehyde

HRID 473437Notes

Reaction equation

HRID 473437 reaction equation
C[CH:2]([C:4]1[C:5]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[S:20]([CH3:23])(=[O:22])=[O:21])=[N:6][C:7]2[C:12]([CH:13]=1)=[N:11][CH:10]=[CH:9][CH:8]=2)[OH:3].[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1>C(Cl)Cl>[CH3:23][S:20]([C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[C:5]1[C:4]([CH:2]=[O:3])=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][N:11]=2)[N:6]=1)(=[O:21])=[O:22]

Participants

4

Reactant 2

HCID 2724130Cornforth reagentHCID 58318628HCID 58318628, compound

Product 1

HCID 583185932-(2-(Methylsulfonyl)phenyl)-1,5-naphthyridine-3-carbaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of crude of methyl (2-(2-(methylsulfonyl)phenyl)-1,5-naphthyridin-3-yl)methanol (1 g, 3.18 mmol) in DCM (10 mL) was added pyridinium dichromate (2.4 g, 6.36 mmol) at 25° C. The reaction mixture was stirred for overnight at same temperature. The reaction mixture was filtered through Celite™. The filtrate was concentrated in vacuo to give 2-(2-(methylsulfonyl)phenyl)-1,5-naphthyridine-3-carbaldehyde: LC-MS (ESI) m/z 313.0 [M+H]+. It was carried on crude for next step.

Workup

  1. filtrationThe reaction mixture was filtered through Celite™
  2. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-d4d5fa77e3f242aea56d38e051f46477
Source dataset
uspto-grants-2014_01
Patent number
US08633313B2

Reaction notes

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