1,4-Dioxane → HCID 58382334, compound

HRID 1628000Notes

Reaction equation

HRID 1628000 reaction equation
[CH2:1]([C:4]1[C:5]([Cl:23])=[C:6]2[CH:12]=[CH:11][N:10]([S:13]([C:16]3[CH:22]=[CH:21][C:19]([CH3:20])=[CH:18][CH:17]=3)(=[O:15])=[O:14])[C:7]2=[N:8][CH:9]=1)[CH:2]=C.[O:24]1CCOCC1>O.CCOC(C)=O.O=[Os](=O)(=O)=O>[Cl:23][C:5]1[C:4]([CH2:1][CH:2]=[O:24])=[CH:9][N:8]=[C:7]2[N:10]([S:13]([C:16]3[CH:22]=[CH:21][C:19]([CH3:20])=[CH:18][CH:17]=3)(=[O:15])=[O:14])[CH:11]=[CH:12][C:6]=12

Participants

6

Reactant 2

HCID 312751,4-DioxaneHCID 58382101HCID 58382101, compound

Product 1

HCID 58382334HCID 58382334, compound

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

5-Allyl-4-chloro-1-tosyl-1H-pyrrolo[2,3-b]pyridine (3.90 g, 11.2 mmol) in 1,4-dioxane (75 mL) and water (15 mL) was treated with NaIO4 (9.62 g, 45.0 mmol) and OsO4 (2.5% in t-BuOH, 5.65 mL, 0.450 mmol). The mixture was stirred at rt for about 1 h then diluted with EtOAc (100 mL). The solids were collected by filtration and the cake was washed with EtOAc (2×100 mL). The filtrate was washed with water (100 mL) and saturated aqueous NaCl (50 mL) then dried over anhydrous MgSO4, filtered and concentrated under reduced pressure. The material was purified by flash chromatography on silica gel to give 2-(4-chloro-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)acetaldehyde as a mixture of aldehyde and hydrate (1.45 g, 37%); LC/MS (Table 2, Method b) Rt=2.51 min; MS m/z 349 (M+H)+.

Workup

  1. filtrationThe solids were collected by filtration
  2. washthe cake was washed with EtOAc (2×100 mL)
  3. washThe filtrate was washed with water (100 mL) and saturated aqueous NaCl (50 mL)
  4. dry with materialthen dried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe material was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-9d244b8e392c422c88d0686bc680c13d
Source dataset
uspto-grants-2014_07
Patent number
US08785639B2

Reaction notes

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