Hydrogen Peroxide → HCID 58955092, compound

HRID 1990971Notes

Reaction equation

[C:1]1([S:7]([C:10]2[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([CH:19]=[CH2:20])[CH:17]=3)[NH:12][CH:11]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.B.C1C[O:25]CC1.[OH-].[Na+].OO>C1COCC1.O>[C:1]1([S:7]([C:10]2[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([CH2:19][CH2:20][OH:25])[CH:17]=3)[NH:12][CH:11]=2)(=[O:8])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 3-(phenylsulfonyl)-5-vinyl-1H-indole (1.9 g, 6.7 mmol) in THF (10 mL) at 0° C. was added dropwise BH3-THF (6.7 mL of 1 M THF solution, 6.7 mmol). The solution was stirred for 3 hours at 0° C., and H2O (7 mL) was added slowly. To this mixture was added 10% NaOH (10 mL), 30% H2O2 and the mixture was stirred vigorously at room temperature for 15 hours. The mixture was partitioned between ethyl acetate and H2O, and the aqueous layer was extracted with ethyl acetate (2×25 mL). The combined organic layers were washed with brine, dried (MgSO4), filtered and concentrated under reduced pressure. Silica gel chromatography (50% ethyl acetate/dichloromethane) gave the title compound as a white solid (1.5 g, 76%). Mp: 55-60° C. MS (ES−): 300 (M−H)

Workup

stirringthe mixture was stirred vigorously at room temperature for 15 hours
customThe mixture was partitioned between ethyl acetate and H2O
extractionthe aqueous layer was extracted with ethyl acetate (2×25 mL)
washThe combined organic layers were washed with brine
dry with materialdried (MgSO4)
filtrationfiltered
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-455afc824d4745449140730b2d65752c
Source dataset: uspto-grants-2010_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07645752B2

Reaction notes

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