2,6-Lutidine → 3-Methyl-1-(phenylsulfonyl)-1H-indole-4-carbaldehyde

HRID 1159780Notes

Reaction equation

HRID 1159780 reaction equation
[CH3:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[CH:11]=C)[N:4]([S:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)(=[O:15])=[O:14])[CH:3]=1.N1C(C)=CC=CC=1C.I([O-])(=O)(=O)=[O:31].[Na+]>O1CCOCC1.O.O=[Os](=O)(=O)=O>[CH3:1][C:2]1[C:10]2[C:9]([CH:11]=[O:31])=[CH:8][CH:7]=[CH:6][C:5]=2[N:4]([S:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)(=[O:15])=[O:14])[CH:3]=1

Participants

7

Reactant 3

HCID 79372,6-LutidineHCID 23667635Sodium periodateHCID 687178803-Methyl-1-(phenylsulfonyl)-4-vinyl-1H-indole3×

Product 1

HCID 866182403-Methyl-1-(phenylsulfonyl)-1H-indole-4-carbaldehydeYield 134.5%

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

OsO4 (29 mg, 0.12 mmol) was added to a stirred mixture of 3-methyl-1-(phenylsulfonyl)-4-vinyl-1H-indole (342 mg, 1.15 mmol; Intermediate 30) and 2,6-lutidine (268 μL, 2.3 mmol) in dioxane (15 mL). The mixture turned from colorless to black in 1 minute. Sodium periodate (0.984 g, 4.6 mmol) in water (5 mL, warmed to dissolve) was added. A grey precipitation was immediately formed. The mixture was stirred for 50 min, combined with an earlier batch of this intermediate (followed this experimental and starting with 3-methyl-1-(phenylsulfonyl)-4-vinyl-1H-indole, 70 mg; Intermediate 30), extracted with water (30 mL) and DCM (2×30 mL). The organic layers were combined, dried, filtered and concentrated to give the title compound (463 mg, 89%) as a black solid. MS (ESI+) for C16H13NO3S m/z 300 (M+H)+.

Workup

  1. customblack in 1 minute
  2. customA grey precipitation
  3. customwas immediately formed
  4. extractionIntermediate 30), extracted with water (30 mL) and DCM (2×30 mL)
  5. customdried
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-e9935d0d5bc34145930daa48e46141b0
Source dataset
uspto-grants-2010_10
Patent number
US07812017B2

Reaction notes

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