2,6-Lutidine → HCID 86618238, compound

HRID 1159771Notes

Reaction equation

HRID 1159771 reaction equation
C[C:2]1[CH:7]=[CH:6]C=C[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].[S:22]1C=CC=C1S(N1C2C(=C(C=C)C=CC=2)C=C1)(=O)=O.N1C(C)=CC=CC=1C.I([O-])(=O)(=O)=O.[Na+]>O=[Os](=O)(=O)=O>[S:22]1[CH:6]=[CH:7][CH:2]=[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]

Participants

6

Reactant 4

HCID 79372,6-LutidineHCID 23667635Sodium periodateHCID 68714627HCID 68714627, compound2×HCID 86618237HCID 86618237, compound

Product 1

HCID 86618238HCID 86618238, compound

Reagents, catalysts & solvents 1

HCID 30318Osmium TetroxideCatalyst

Procedure

The experimental for Intermediate 16 was followed using 1-(2-thienylsulfonyl)-4-vinyl-1H-indole (333 mg, 1.15 mmol; Intermediate 21), OsO4 (15 mg, 0.06 mmol), 2,6-lutidine (268 μL, 2.30 mmol) and sodium periodate (0.984 g, 4.60 mmol). The title compound was obtained (306 mg, 91%, still some dioxane according to HNMR) as a black gum. MS (ESI+) for C13H9NO3S2 m/z 292 (M+H)+.

Sources & evidence

ORD record
ord-d94e9fe016ea4c699ad736a1056ec61c
Source dataset
uspto-grants-2010_10
Patent number
US07812017B2

Reaction notes

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