2,6-Lutidine → 1-[(2-Methoxy-5-methylphenyl)sulfonyl]indoline-4-carbaldehyde

HRID 1159761Notes

Reaction equation

HRID 1159761 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)[CH2:15][CH2:14]1)(=[O:12])=[O:11].N1C(C)=CC=CC=1C.I([O-])(=O)(=O)=[O:33].[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:33])[C:16]=2[CH2:15][CH2:14]1)(=[O:11])=[O:12]

Participants

7

Reactant 3

HCID 79372,6-LutidineHCID 23667635Sodium periodateHCID 687143621-[(2-Methoxy-5-methylphenyl)sulfonyl]-4-vinylindoline3×

Product 1

HCID 866182351-[(2-Methoxy-5-methylphenyl)sulfonyl]indoline-4-carbaldehyde

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

OsO4 (9 mg, 0.05 mmol) was added to a stirred mixture of 1-[(2-methoxy-5-methylphenyl)sulfonyl]-4-vinylindoline (240 mg, 0.73 mmol; Intermediate 10) and 2,6-lutidine (170 μL, 1.46 mmol) in dioxane (12 mL). The mixture turned from colorless to black in 1 minute. Sodium periodate (0.625 g, 2.92 mmol) in water (4 mL, warmed to dissolve) was added. A grey precipitation was immediately formed. The mixture was stirred for 25 min, combined with an earlier batch of this intermediate (followed this experimental and starting from Intermediate 10; 60 mg, 18 mmol), 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 (360 mg, still some dioxane according to HNMR) as a black sticky oil. MS (ESI+) for C17H17NO4S m/z 332 (M+H)+.

Workup

  1. customblack in 1 minute
  2. customA grey precipitation
  3. customwas immediately formed
  4. custom60 mg, 18 mmol), and partitioned 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-a3fa88767036422f9dc099d0ad267328
Source dataset
uspto-grants-2010_10
Patent number
US07812017B2

Reaction notes

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