Hydrogen Peroxide → HCID 86686450, compound

HRID 2176813Notes

Reaction equation

HRID 2176813 reaction equation
[F:1][C:2]([F:24])([F:23])[S:3]([O:6][C:7]1[C:8]([S:21][CH3:22])=[C:9]2[C:13](=[CH:14][CH:15]=1)[N:12]([CH:16]([CH2:18][CH2:19][CH3:20])[CH3:17])[CH:11]=[CH:10]2)(=[O:5])=[O:4].[OH:25]O>C(O)(=O)C>[F:24][C:2]([F:1])([F:23])[S:3]([O:6][C:7]1[C:8]([S:21]([CH3:22])=[O:25])=[C:9]2[C:13](=[CH:14][CH:15]=1)[N:12]([CH:16]([CH2:18][CH2:19][CH3:20])[CH3:17])[CH:11]=[CH:10]2)(=[O:5])=[O:4]

Participants

4

Reactant 2

HCID 784Hydrogen PeroxideHCID 86686451HCID 86686451, compound

Product 1

HCID 86686450HCID 86686450, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 4-(methylthio)-1-(pentan-2-yl)-1H-indol-5-yltrifluoromethanesulfonate (13) (1.3 g, 3.4 mmol) in acetic acid (CH3COOH, 5.0 mL) at around 5° C. was added hydrogen peroxide (H2O2, 30%, 0.42 ml, 3.7 mmol). The mixture was allowed to warm to room temperature, stirred overnight, and then concentrated to dryness in vacuo to give 4-(methylsulfinyl)-1-(pentan-2-yl)-1H-indol-5-yl trifluoromethanesulfonate (17) (1.32 g, 100%). 1H NMR (500 MHz, CD2Cl2): δ 7.58 (d, J=9.0, 1H), 7.45 (d, J=2.5 Hz, 1H), 7.35 (m, 1H), 7.13 (d, J=9.0, 1H), 4.57 (m, 1H), 3.07 (d, 3H), 1.87 (m, 2H), 1.55 (m, 3H), 1.26 (m, 2H), 0.92 (m, 3H). Mass (ESI, M+H): 398.4. See also Bronner, S. M.; Bahnck K. B.; Garg, N. K.; Org. Lett., 11: 1007 (2009).

Workup

  1. concentrationconcentrated to dryness in vacuo

Sources & evidence

ORD record
ord-d5f3cf29aeaa4c318d0c7bdf9b44cee1
Source dataset
uspto-grants-2015_06
Patent number
US09067886B2

Reaction notes

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