Sodium periodate → 1-[(2-Methoxy-5-methylphenyl)sulfonyl]-1H-indole-4-carbaldehyde

HRID 1159758Notes

Reaction equation

HRID 1159758 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH3:9])=[CH:5][C:4]=1[S:10]([N:13]1[C:21]2[C:16](=[C:17]([CH:22]=C)[CH:18]=[CH:19][CH:20]=2)[CH:15]=[CH:14]1)(=[O:12])=[O:11].I([O-])(=O)(=O)=[O:25].[Na+]>O1CCOCC1.O.O=[Os](=O)(=O)=O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH3:9])=[CH:5][C:4]=1[S:10]([N:13]1[C:21]2[CH:20]=[CH:19][CH:18]=[C:17]([CH:22]=[O:25])[C:16]=2[CH:15]=[CH:14]1)(=[O:12])=[O:11]

Participants

6

Reactant 2

HCID 23667635Sodium periodateHCID 687165841-[(2-Methoxy-5-methylphenyl)sulfonyl]-4-vinyl-1H-indole2×

Product 1

HCID 866182341-[(2-Methoxy-5-methylphenyl)sulfonyl]-1H-indole-4-carbaldehyde

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

OsO4 (10 mg, 0.05 mmol) was added to a stirred mixture of 1-[(2-methoxy-5-methylphenyl)sulfonyl]-4-vinyl-1H-indole (262 mg, 0.80 mmol; Intermediate 7) and 2,6-2,6-lutidine (186 μL, 0.46 mmol) in dioxane (9 mL). The mixture turned from colorless to black in 1 minute. Sodium periodate (0.684 g, 3.2 mmol) in water (3 mL, warmed to dissolve) was added. A grey precipitation was immediately formed. The mixture was stirred for 30 min. and partitioned between 2M aqueous HCl (25 mL) and DCM (25 mL). The organic layer was dried, filtered and concentrated to give the title compound (290 mg, 110%, still some dioxane according to HNMR) as a black solid. MS (ESI+) for C17H15NO4S m/z 330 (M+H)+.

Workup

  1. customblack in 1 minute
  2. customA grey precipitation
  3. customwas immediately formed
  4. custompartitioned between 2M aqueous HCl (25 mL) and DCM (25 mL)
  5. customThe organic layer was dried
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-d3ed68de8d434844847ebd25c33d68c4
Source dataset
uspto-grants-2010_10
Patent number
US07812017B2

Reaction notes

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