2,6-Lutidine → 1-[(4-Fluorophenyl)sulfonyl]-1H-indole-4-carbaldehyde

HRID 1159762Notes

Reaction equation

HRID 1159762 reaction equation
CO[C:3]1[CH:8]=[CH:7][C:6](C)=[CH:5][C:4]=1[S:10]([N:13]1[C:21]2[CH:20]=[CH:19][CH:18]=[C:17]([CH:22]=[O:23])[C:16]=2[CH:15]=[CH:14]1)(=[O:12])=[O:11].[F:24]C1C=CC(S(N2C3C(=C(C=C)C=CC=3)C=C2)(=O)=O)=CC=1.N1C(C)=CC=CC=1C.I([O-])(=O)(=O)=O.[Na+]>O=[Os](=O)(=O)=O.O1CCOCC1.O>[F:24][C:7]1[CH:6]=[CH:5][C:4]([S:10]([N:13]2[C:21]3[CH:20]=[CH:19][CH:18]=[C:17]([CH:22]=[O:23])[C:16]=3[CH:15]=[CH:14]2)(=[O:12])=[O:11])=[CH:3][CH:8]=1

Participants

8

Reactant 4

HCID 79372,6-LutidineHCID 23667635Sodium periodateHCID 687142381-[(4-fluorophenyl)sulfonyl]-4-vinyl-1H-indole2×HCID 866182341-[(2-Methoxy-5-methylphenyl)sulfonyl]-1H-indole-4-carbaldehyde

Product 1

HCID 866182361-[(4-Fluorophenyl)sulfonyl]-1H-indole-4-carbaldehyde

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent2×

Procedure

The procedure for Intermediate 8 was followed using OsO4 (15 mg, 0.058 mmol), 1-[(4-fluorophenyl)sulfonyl]-4-vinyl-1H-indole (347 mg, 1.15 mmol; Intermediate 12), 2,6-lutidine (268 μL, 2.3 mmol), dioxane (15 mL), sodium periodate (0.984 g, 4.6 mmol) and water (5 mL). The title compound (360 mg, 103%, still some dioxane according to HNMR) was obtained as a black sticky oil. MS (ESI+) for C15H10FNO3S m/z 304 (M+H)+.

Sources & evidence

ORD record
ord-610c575ba4c0477aa2848083eb323d8b
Source dataset
uspto-grants-2010_10
Patent number
US07812017B2

Reaction notes

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