Cornforth reagent → HCID 58318632, compound

HRID 473429Notes

Reaction equation

HRID 473429 reaction equation
C[CH:2]([C:4]1[C:5]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[S:21]([CH3:24])(=[O:23])=[O:22])=[N:6][C:7]2[C:12]([CH:13]=1)=[N:11][CH:10]=[C:9]([F:14])[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>[F:14][C:9]1[CH:8]=[C:7]2[C:12]([CH:13]=[C:4]([CH:2]=[O:3])[C:5]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[S:21]([CH3:24])(=[O:23])=[O:22])=[N:6]2)=[N:11][CH:10]=1

Participants

4

Reactant 2

HCID 2724130Cornforth reagentHCID 58318610HCID 58318610, compound

Product 1

HCID 58318632HCID 58318632, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl (7-fluoro-2-(2-(methylsulfonyl)phenyl)-1,5-naphthyridin-3-yl)methanol (50 mg, 0.15 mmol) in DCM (0.5 mL) was added pyridinium dichromate (113 mg, 0.3 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 7-fluoro-2-(2-(methylsulfonyl)phenyl)-1,5-naphthyridine-3-carbaldehyde: LC-MS (ESI) m/z 331.1 [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-24569e3ed17d43f7952eef3ca216d340
Source dataset
uspto-grants-2014_01
Patent number
US08633313B2

Reaction notes

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