2,6-Lutidine → HCID 18973459, compound

HRID 1159768Notes

Reaction equation

HRID 1159768 reaction equation
C[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:21])[C:14]=2[CH:13]=[CH:12]1)(=[O:10])=[O:9].[F:22][C:23]([F:45])([F:44])C1C=C(S(N2C3C(=C(C=C)C=CC=3)C=C2)(=O)=O)C=CC=1.N1C(C)=CC=CC=1C.I([O-])(=O)(=O)=O.[Na+]>O=[Os](=O)(=O)=O>[F:22][C:23]([F:45])([F:44])[C:5]1[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:9])=[O:10])[CH:2]=[CH:7][CH:6]=1

Participants

6

Reactant 4

HCID 79372,6-LutidineHCID 23667635Sodium periodateHCID 687142331-{[3-(Trifluoromethyl)phenyl]sulfonyl}-4-vinyl-1H-indole2×HCID 86618237HCID 86618237, compound

Product 1

HCID 18973459HCID 18973459, compound

Reagents, catalysts & solvents 1

HCID 30318Osmium TetroxideCatalyst

Procedure

The experimental for Intermediate 16 was followed using 1-{[3-(trifluoromethyl)phenyl]sulfonyl}-4-vinyl-1H-indole (348 mg, 0.99 mmol; Intermediate 18), OsO4 (13 mg, 0.05 mmol), 2,6-lutidine (230 μL, 2.0 mmol) and sodium periodate (0.848 g, 3.96 mmol). The title compound was obtained (368 mg, 105%, still some dioxane according to HNMR) as a black gum. MS (ESI+) for C16H10F3NO3S m/z 354 (M+H)+.

Sources & evidence

ORD record
ord-c1997dcd84c74656b5a3f0ddeadf17e1
Source dataset
uspto-grants-2010_10
Patent number
US07812017B2

Reaction notes

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