Triacetoxyperiodinane → 6-(2,4-difluorophenyl)-1-(2,6-difluorophenyl)-2-oxo-2H-quinolizine-7-carbaldehyde

HRID 1360712Notes

Reaction equation

HRID 1360712 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:10]2[C:15]([CH:16]=[CH:17][C:18]=1[CH2:19][O:20]C)=[C:14]([C:22]1[C:27]([F:28])=[CH:26][CH:25]=[CH:24][C:23]=1[F:29])[C:13](=[O:30])[CH:12]=[CH:11]2.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:10]2[C:15]([CH:16]=[CH:17][C:18]=1[CH:19]=[O:20])=[C:14]([C:22]1[C:23]([F:29])=[CH:24][CH:25]=[CH:26][C:27]=1[F:28])[C:13](=[O:30])[CH:12]=[CH:11]2

Participants

3

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 160653126-(2,4-difluorophenyl)-1-(2,6-difluorophenyl)-7-(methoxymethyl)-2H-quinolizin-2-one

Product 1

HCID 160653166-(2,4-difluorophenyl)-1-(2,6-difluorophenyl)-2-oxo-2H-quinolizine-7-carbaldehydeYield 39.6%

Procedure

To a solution of 6-(2,4-difluorophenyl)-1-(2,6-difluorophenyl)-7-(hydroxymethyl)-2H-quinolizin-2-one (Example 52, 21 mg) was added Dess-Martin periodinane (30 mg) at room temperature and stirred for 12 h. The mixture was concentrated and purified by silica gel (methylene chloride/methanol=20/1) to give the title compound (8 mg).

Workup

  1. concentrationThe mixture was concentrated
  2. custompurified by silica gel (methylene chloride/methanol=20/1)

Sources & evidence

ORD record
ord-bf329f5d4b6846b6af57654602f21b45
Source dataset
uspto-grants-2011_02
Patent number
US07879875B2

Reaction notes

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