2,6-Lutidine → HCID 86618242, compound

HRID 1159786Notes

Reaction equation

HRID 1159786 reaction equation
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][N:8]2[S:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)(=[O:13])=[O:12])=[C:4]([CH:20]=C)[CH:3]=1.N1C(C)=CC=CC=1C.I([O-])(=O)(=O)=[O:31].[Na+]>O1CCOCC1.O.O=[Os](=O)(=O)=O>[F:1][C:2]1[CH:3]=[C:4]([CH:20]=[O:31])[C:5]2[CH:6]=[CH:7][N:8]([S:11]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)(=[O:13])=[O:12])[C:9]=2[CH:10]=1

Participants

7

Reactant 3

HCID 79372,6-LutidineHCID 23667635Sodium periodateHCID 68715502HCID 68715502, compound2×

Product 1

HCID 86618242HCID 86618242, compoundYield 105%

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

OsO4 (26 mg, 0.1 mmol) was added to a stirred mixture of 6-fluoro-1-(phenylsulfonyl)-4-vinyl-1H-indole (309 mg, 1.03 mmol; Intermediate 37) and 2,6-lutidine (239 μL, 2.05 mmol) in dioxane (18 mL). The mixture turned from colorless to black in 1 minute. Sodium periodate (0.877 g, 4.1 mmol) in water (6 mL, warmed to dissolve) was added. A grey precipitation was immediately formed. The mixture was stirred for 15 min, extracted with water (30 mL) and DCM (2×30 mL). The organic layers were combined, dried, filtered and concentrated to give the title compound (326 mg, 105%) as a black solid. MS (ESI+) for C15H10FNO3S m/z 304 (M+H)+.

Workup

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

Sources & evidence

ORD record
ord-99f8ac599e7b488d814aed9f8dc34e4f
Source dataset
uspto-grants-2010_10
Patent number
US07812017B2

Reaction notes

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