Indole-5-carbonitrile, 3-(2-aminoethyl)-, hydrochloride → N-t-Butoxycarbonyl-2-(5-cyano-1H-indol-3-yl)ethylamine
Reaction equation
Cl.[NH2:2][CH2:3][CH2:4][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([C:14]#[N:15])[CH:12]=2)[NH:7][CH:6]=1.Cl.[C:17]([C:19]1[CH:24]=CC(NN)=C[CH:20]=1)#N.CCCCCC.[C:33]([O:36]CC)(=[O:35])C>>[C:19]([O:36][C:33]([NH:2][CH2:3][CH2:4][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([C:14]#[N:15])[CH:12]=2)[NH:7][CH:6]=1)=[O:35])([CH3:24])([CH3:20])[CH3:17]Participants
4
Procedure
The title compound was prepared in 58% yield from 3-(2-aminoethyl)-5-cyano-1H-indole hydrochloride using the conditions described for Intermediate 1 (Step 3); white solid; mp 132°-134° C. (hexane-ethyl acetate); δH (250 MHz, CDCl3) 8.42 (1H, br s, indole N--H), 7.93 (1H, s, Ar--H), 7.41 (2H, s, Ar--H), 7.12 (1H, d, J=2.2 Hz, Ar--H), 4.71 (1H, br s, --NH--), 3.44 (2H, q, J=6.9 Hz, --CH2NH--), 2.94 (2H, t, J=6.9 Hz, Ar--CH2 --), 1.45 (9H, s, t-Bu); m/z (CI) 286 (M+ +1).
Sources & evidence
- ORD record
- ord-2f71d690067d4e7a96e02d81383bde61
- Source dataset
- uspto-grants-1993_03
- Patent number
- US05194440
Reaction notes
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