Iodine → HCID 58955097, compound

HRID 1990982Notes

Reaction equation

[NH:1]1[C:9]2[C:4](=[C:5]([CH2:10][CH2:11][CH2:12][OH:13])[CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[C:14]1([SH:20])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[I-].[K+].II>C(O)C.O.C(OCC)(=O)C>[C:14]1([S:20][C:3]2[C:4]3[C:9](=[CH:8][CH:7]=[CH:6][C:5]=3[CH2:10][CH2:11][CH2:12][OH:13])[NH:1][CH:2]=2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

Conditions

Temperature: 65 °C

Procedure

To a solution of 3-(1H-indol-4-yl)propan-1-ol (0.91 g, 5.19 mmol) and thiophenol (0.53 mL, 5.19 mmol) in absolute ethanol (30 mL) was added a solution of potassium iodide (0.862 g, 5.19 mmol) and iodine (1.318 g, 5.19 mmol) in ethanol (7.5 mL) and water (22.5 mL) over 5 minutes, and the reaction was then heated at 65° C. for 5.5 hours. The cooled reaction mixture was diluted with ethyl acetate (250 mL), washed with 5% aqueous Na2S2O3 solution (250 mL), water (250 mL) and brine (250 mL), dried (Na2SO4), filtered and concentrated in vacuo to afford an off-white solid. Purification by flash chromatography (25 to 75% ethyl acetate/hexane) afforded a white solid. The product was recrystallized from 3:1 v/v hexane:ethyl acetate (60 mL) to afford the title compound as a white crystalline solid (1.048 g, 71%). MS (ES+) m/z 284.1 (M+H).

Workup

customThe cooled reaction mixture
washwashed with 5% aqueous Na2S2O3 solution (250 mL), water (250 mL) and brine (250 mL)
dry with materialdried (Na2SO4)
filtrationfiltered
concentrationconcentrated in vacuo
customto afford an off-white solid
customPurification by flash chromatography (25 to 75% ethyl acetate/hexane)
customafforded a white solid
customThe product was recrystallized from 3:1 v/v hexane

Sources & evidence

ORD record: ord-bcbaac58345c42a6824a70abd0bfec6a
Source dataset: uspto-grants-2010_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07645752B2

Reaction notes

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