Styrene → 2-(1-Ethyl-6-isopropyl-8-styryl-1,3,4,9-tetrahydro-pyrano[3,4-b]indol-1-yl)-ethanol

HRID 268661Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]([CH:20]([CH3:22])[CH3:21])[CH:5]=[C:6]2[C:10]=1[NH:9][C:8]1[C:11]([CH2:17][CH2:18][OH:19])([CH2:15][CH3:16])[O:12][CH2:13][CH2:14][C:7]2=1.C(N(CC)CC)C.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.[CH2:52]=[CH:53][C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1>C(#N)C>[CH2:15]([C:11]1([CH2:17][CH2:18][OH:19])[C:8]2[NH:9][C:10]3[C:6]([C:7]=2[CH2:14][CH2:13][O:12]1)=[CH:5][C:4]([CH:20]([CH3:22])[CH3:21])=[CH:3][C:2]=3[CH:52]=[CH:53][C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1)[CH3:16]

Participants

Conditions

Temperature: 90 °C

Procedure

The title compound is prepared according to the following procedure. To solution of 2-(8-bromo-1-ethyl-6-isopropyl-1,3,4,9-tetrahydro-pyrano[3,4-b]indol-1-yl)-ethanol (1.0 mmol) in dried acetonitril (10 mL) at under nitrogen is added triethylamine (1.5 mL), tri-o-tolylphosphine (0.4 mmol), styrene (2.0 mmol), and tri(dibenzylideneacetone)dipalladiumn (0) (0.1 mmol). The reaction mixture is heated at 90° C. (oil bath) overnight. It is quenched with water and extracted with ethyl acetate. Extracts are dried over magnesium sulfate and concentrated under reduced pressure. The chromatography (silica gel) gives the title compound.

Workup

customThe title compound is prepared
customIt is quenched with water
extractionextracted with ethyl acetate
dry with materialExtracts are dried over magnesium sulfate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-9fbab4f83e604f508c13e7940a4a97f6
Source dataset: uspto-grants-2008_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07446122B2

Reaction notes

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