Sodium periodate → HCID 86697085, compound

HRID 626811Notes

Reaction equation

HRID 626811 reaction equation
[Cl:1][C:2]1[C:3]([N:12]2[CH:29]=[C:15]3[C:16]([NH:21][C:22]4[CH:27]=[C:26]([CH3:28])[N:25]=[CH:24][N:23]=4)=[N:17][CH:18]=[C:19]([F:20])[C:14]3=[N:13]2)=[C:4]([CH:7]=[C:8]([CH:10]=C)[CH:9]=1)[C:5]#[N:6].I([O-])(=O)(=O)=[O:31].[Na+]>CC(C)=O.O.[Os](=O)(=O)(=O)=O>[Cl:1][C:2]1[C:3]([N:12]2[CH:29]=[C:15]3[C:16]([NH:21][C:22]4[CH:27]=[C:26]([CH3:28])[N:25]=[CH:24][N:23]=4)=[N:17][CH:18]=[C:19]([F:20])[C:14]3=[N:13]2)=[C:4]([CH:7]=[C:8]([CH:10]=[O:31])[CH:9]=1)[C:5]#[N:6]

Participants

6

Reactant 2

HCID 23667635Sodium periodateHCID 69671365HCID 69671365, compound

Product 1

HCID 86697085HCID 86697085, compoundYield 60%

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalystHCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

Osmium (VIII) oxide (2.5% wt in tert-butanol, 0.1 mL) was added to a solution of 3-chloro-2-[7-fluoro-4-(6-methylpyrimidin-4-ylamino)pyrazolo[4,3-c]pyridin-2-yl]-5-vinylbenzonitrile (42 mg, 0.1 mmol) in acetone (2.0 mL) and water (0.5 mL). Sodium periodate (47 mg, 0.22 mmol) was then added and the reaction mixture was stirred at room temperature overnight. The resultant mixture was partitioned between ethyl acetate and water and the layers were separated. The organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel flash chromatography (70-80% ethyl acetate in cyclohexane) to afford the title compound as a yellow glass (24 mg, 60% yield). 1H NMR (400 MHz, DMSO-d6): δ 10.89 (s, 1H), 10.12 (s, 1H), 9.55 (d, J=2.5 Hz, 1H), 8.72-8.62 (m, 3H), 8.37 (s, 1H), 8.03 (d, J=3.4 Hz, 1H), 2.45 (s, 3H).

Workup

  1. customThe resultant mixture was partitioned between ethyl acetate and water
  2. customthe layers were separated
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel flash chromatography (70-80% ethyl acetate in cyclohexane)

Sources & evidence

ORD record
ord-1818ac0c18354731855b512ec426e3b3
Source dataset
uspto-grants-2016_04
Patent number
US09309240B2

Reaction notes

Loading…