Cornforth reagent → HCID 68183178, compound

HRID 513659Notes

Reaction equation

HRID 513659 reaction equation
C1C=C[NH+]=CC=1.C1C=C[NH+]=CC=1.[O-][Cr](O[Cr]([O-])(=O)=O)(=O)=O.[F:22][C:23]1[CH:28]=[CH:27][C:26]([CH:29]([C:31]2[C:40]([N+:41]([O-:43])=[O:42])=[C:39]3[C:34]([CH:35]=[CH:36][CH:37]=[N:38]3)=[CH:33][CH:32]=2)[OH:30])=[CH:25][CH:24]=1>C(Cl)Cl>[F:22][C:23]1[CH:24]=[CH:25][C:26]([C:29]([C:31]2[C:40]([N+:41]([O-:43])=[O:42])=[C:39]3[C:34]([CH:35]=[CH:36][CH:37]=[N:38]3)=[CH:33][CH:32]=2)=[O:30])=[CH:27][CH:28]=1

Participants

4

Reactant 2

HCID 2724130Cornforth reagentHCID 68183177HCID 68183177, compound2×

Product 1

HCID 68183178HCID 68183178, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
30 °C

Procedure

PDC (404 mg, 1.08 mmol) was added to a solution of (4-fluoro-phenyl)-(8-nitro-quinolin-7-yl)-methanol (Intermediate 337) (214 mg, 0.72 mmol) in DCM (10 ml). The mixture was heated to 30° C. and stirring was continued for 18 h. After cooling, the mixture was concentrated in vacuo. The crude residue was dissolved in toluene, filtered and concentrated in vacuo to give the title compound (160 mg, 75%).

Workup

  1. temperatureAfter cooling
  2. concentrationthe mixture was concentrated in vacuo
  3. dissolutionThe crude residue was dissolved in toluene
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e400562dc5494e828048ad93db15e5f4
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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