2,6-Lutidine → HCID 86618237, compound

HRID 1159765Notes

Reaction equation

HRID 1159765 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([N:11]1[C:19]2[C:14](=[C:15]([CH:20]=C)[CH:16]=[CH:17][CH:18]=2)[CH:13]=[CH:12]1)(=[O:10])=[O:9].N1C(C)=CC=CC=1C.I([O-])(=O)(=O)=[O:31].[Na+]>O1CCOCC1.O.O=[Os](=O)(=O)=O>[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([N:11]1[C:19]2[CH:18]=[CH:17][CH:16]=[C:15]([CH:20]=[O:31])[C:14]=2[CH:13]=[CH:12]1)(=[O:10])=[O:9]

Participants

7

Reactant 3

HCID 79372,6-LutidineHCID 23667635Sodium periodateHCID 68713053HCID 68713053, compound2×

Product 1

HCID 86618237HCID 86618237, compound

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

OsO4 (15 mg, 0.06 mmol) was added to a stirred mixture of 1-[(2-methylphenyl)sulfonyl]-4-vinyl-1H-indole (300 mg, 1.01 mmol; Intermediate 15) and 2,6-lutidine (235 μl, 2.02 mmol) in dioxane (24 mL). The mixture turned from colorless to black in 3 minutes. Sodium periodate (0.865 g, 4.04 mmol) in water (8 mL, warmed to dissolve) was added. A grey precipitation was immediately formed. The mixture was stirred for 1.40 h and extracted with 2M aqueous HCl (25 mL) and DCM (2×25 mL). The organic layers were combined, dried, filtered and concentrated to give the title compound (358 mg, 118%, still some dioxane according to HNMR) as a black gum. MS (ESI+) for C16H13NO3S m/z 300 (M+H)+.

Workup

  1. customA grey precipitation
  2. customwas immediately formed
  3. extractionextracted with 2M aqueous HCl (25 mL) and DCM (2×25 mL)
  4. customdried
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-d0bfe57182cb41039c688af13d2226bb
Source dataset
uspto-grants-2010_10
Patent number
US07812017B2

Reaction notes

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