Propan-2-one--water (1/1) → 8-Fluoro-2-(2-isopropyl-5-methyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-1,3a-diazabenzo[e]azulene-9-carbaldehyde

HRID 1530729Notes

Reaction equation

HRID 1530729 reaction equation
I([O-])(=O)(=O)=O.[Na+].[F:7][C:8]1[C:30]([CH:31]=C)=[CH:29][C:11]2[C:12]3[N:16]([CH2:17][CH2:18][O:19][C:10]=2[CH:9]=1)[CH:15]=[C:14]([C:20]1[N:21]([CH:26]([CH3:28])[CH3:27])[N:22]=[C:23]([CH3:25])[N:24]=1)[N:13]=3.CC(C)=[O:35].O>CC(O)(C)C.CCOC(C)=O.[Os](=O)(=O)(=O)=O>[F:7][C:8]1[C:30]([CH:31]=[O:35])=[CH:29][C:11]2[C:12]3[N:16]([CH2:17][CH2:18][O:19][C:10]=2[CH:9]=1)[CH:15]=[C:14]([C:20]1[N:21]([CH:26]([CH3:28])[CH3:27])[N:22]=[C:23]([CH3:25])[N:24]=1)[N:13]=3

Participants

7

Reactant 3

HCID 18366337Propan-2-one--water (1/1)HCID 23667635Sodium periodateHCID 683126378-Fluoro-2-(2-isopropyl-5-methyl-2H-[1,2,4]triazol-3-yl)-9-vinyl-4,5-dihydro-6-oxa-1,3a-diazabenzo[e]azulene

Product 1

HCID 866714868-Fluoro-2-(2-isopropyl-5-methyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-1,3a-diazabenzo[e]azulene-9-carbaldehydeYield 96%

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalystHCID 6386tert-ButanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

Osmium tetraoxide (1.8 mL of a 2.5% solution in tBuOH) and sodium periodate (1.51 g, 7.08 mmol) were added to a solution of 8-fluoro-2-(2-isopropyl-5-methyl-2H-[1,2,4]triazol-3-yl)-9-vinyl-4,5-dihydro-6-oxa-1,3a-diazabenzo[e]azulene (1.0 g, 2.83 mmol) in an acetone-water mixture (5:1, 60 mL). The reaction mixture was stirred vigorously for 24 h at RT. The mixture was diluted with EtOAc (100 mL), washed with water and brine, dried (Na2SO4) and concentrated in vacuo to give the title compound (968 mg, 2.72 mmol, 96%) as a pale yellow oil. The product was taken on without further purification. LCMS (Method J): RT=2.78 min, [M+H]+ =356

Workup

  1. washwashed with water and brine
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-70f2cde89e9a40cea031568e153f336f
Source dataset
uspto-grants-2015_07
Patent number
US09090628B2

Reaction notes

Loading…