2,6-Lutidine → HCID 86618239, compound

HRID 1159775Notes

Reaction equation

HRID 1159775 reaction equation
C[C:2]1C=[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:21])[C:14]=2[CH:13]=[CH:12]1)(=[O:10])=[O:9].[N:22]1C=CC=C(S(N2C3C(=C(C=C)C=CC=3)C=C2)(=O)=O)C=1.N1C(C)=CC=CC=1C.I([O-])(=O)(=O)=O.[Na+]>O=[Os](=O)(=O)=O>[N:22]1[CH:6]=[CH:5][CH:4]=[C:3]([S:8]([N:11]2[C:19]3[CH:18]=[CH:17][CH:16]=[C:15]([CH:20]=[O:21])[C:14]=3[CH:13]=[CH:12]2)(=[O:10])=[O:9])[CH:2]=1

Participants

6

Reactant 4

HCID 79372,6-LutidineHCID 23667635Sodium periodateHCID 68717796HCID 68717796, compound2×HCID 86618237HCID 86618237, compound

Product 1

HCID 86618239HCID 86618239, compound

Reagents, catalysts & solvents 1

HCID 30318Osmium TetroxideCatalyst

Procedure

The experimental for Intermediate 16 was followed using 1-(pyridine-3-ylsulfonyl)-4-vinyl-1H-indole (208 mg, 0.73 mmol; Intermediate 25), OsO4 (9 mg, 0.04 mmol), 2,6-lutidine (170 μL, 1.46 mmol) and sodium periodate (0.625 g, 2.92 mmol). After flash purification by flash chromatography, some material was insoluble in DCM/MeOH and filtered off. The title compound (123 mg, 59%, still some dioxane according to HNMR) was obtained as a black gum. MS (ESI+) for C14H10N2O3S m/z 287 (M+H)+.

Workup

  1. customAfter flash purification by flash chromatography
  2. filtrationfiltered off

Sources & evidence

ORD record
ord-5e73dd4c05eb4c3392589acf78bf7e1d
Source dataset
uspto-grants-2010_10
Patent number
US07812017B2

Reaction notes

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