2,6-Lutidine → 1-Tosyl-1H-indole-4-carbaldehyde

HRID 1159755Notes

Reaction equation

HRID 1159755 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[C:19]3[C:14](=[C:15]([CH:20]=C)[CH:16]=[CH:17][CH:18]=3)[CH:13]=[CH:12]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.N1C(C)=CC=CC=1C.[O:30]1CCOCC1.I([O-])(=O)(=O)=O.[Na+]>O=[Os](=O)(=O)=O.O>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[C:19]3[CH:18]=[CH:17][CH:16]=[C:15]([CH:20]=[O:30])[C:14]=3[CH:13]=[CH:12]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 79372,6-LutidineHCID 312751,4-DioxaneHCID 124465911-[(4-Methylphenyl)sulfonyl]-4-vinyl-1H-indole2×HCID 23667635Sodium periodate

Product 1

HCID 131150931-Tosyl-1H-indole-4-carbaldehydeYield 99%

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolvent

Procedure

The experimental for Intermediate 5 Batch 1 was followed using OsO4 (27 mg, 0.11 mmol), 1-[(4-methylphenyl)sulfonyl]-4-vinyl-1H-indole (0.321 g, 1.08 mmol; Intermediate 4), 2,6-lutidine (0.251 mL, 0.23 mmol), dioxane (12 mL), sodium periodate (0.924 g, 4.32 mmol) and water (4 mL). The mixture was stirred for 20 min. and partitioned between 2M aqueous HCl (25 mL) and DCM (25 mL). The organic layer was dried, filtered, combined with Intermediate 5 Batch 1, and concentrated to give a total yield of 390 mg, 99% of a black solid. MS (ESI+) for C16H13NO3S m/z 300 (M+H)+.

Workup

  1. custompartitioned between 2M aqueous HCl (25 mL) and DCM (25 mL)
  2. customThe organic layer was dried
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-4a12cd9d6a3349c99da6cf1109ae06d2
Source dataset
uspto-grants-2010_10
Patent number
US07812017B2

Reaction notes

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