Ethyl Acetate → 1-(4-Cyanobutyl)-3-indolecarboxylic acid benzyl ester

HRID 725907Notes

Reaction equation

Br[CH2:2][CH2:3][CH2:4][CH2:5][C:6]#[N:7].[CH2:8]([O:15][C:16]([C:18]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[NH:20][CH:19]=1)=[O:17])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[H-].[Na+].C(OCC)(=O)C>O1CCCC1.O>[CH2:8]([O:15][C:16]([C:18]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[N:20]([CH2:2][CH2:3][CH2:4][CH2:5][C:6]#[N:7])[CH:19]=1)=[O:17])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

Conditions

Temperature: 0 °C

Procedure

1.1 equivalents of 5-bromovaleronitrile are added to 40 mmol of 3-indolecarboxylic acid benzyl ester dissolved in tetrahydrofuran. After cooling to 0° C., 1.8 g of sodium hydride are added portionwise. After one hour of reaction at 0° C. and 14 hours at room temperature, ethyl acetate and water are added. The organic phase is separated and washed several times in succession with an aqueous phase containing hydrochloric acid followed by a basic aqueous phase. After drying and evaporation, the residue is purified by chromatography on silica gel using an ethyl acetate/pentane (2:3) mixture as solvent, and the expected product is obtained.

Workup

customAfter one hour of reaction at 0° C.
customThe organic phase is separated
washwashed several times in succession with an aqueous phase
additioncontaining hydrochloric acid
customAfter drying
customevaporation
customthe residue is purified by chromatography on silica gel using an ethyl acetate/pentane (2:3) mixture as solvent

Sources & evidence

ORD record: ord-fa4574a72e6f46cf85b585d99d246735
Source dataset: uspto-grants-1998_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05708016

Reaction notes

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