4-Cyanophenylboronic acid → (rac)-4-(8-Hydroxy-5,6,7,8-tetrahydroisoquinolin-4-yl)benzonitrile

HRID 714070Notes

Reaction equation

HRID 714070 reaction equation
Br[C:2]1[C:11]2[CH2:10][CH2:9][CH2:8][CH:7]([OH:12])[C:6]=2[CH:5]=[N:4][CH:3]=1.[C:13]([C:15]1[CH:20]=[CH:19][C:18](B(O)O)=[CH:17][CH:16]=1)#[N:14]>>[OH:12][CH:7]1[C:6]2[CH:5]=[N:4][CH:3]=[C:2]([C:18]3[CH:19]=[CH:20][C:15]([C:13]#[N:14])=[CH:16][CH:17]=3)[C:11]=2[CH2:10][CH2:9][CH2:8]1

Participants

3

Reactant 2

HCID 27343264-Cyanophenylboronic acidHCID 717438914-Bromo-5,6,7,8-tetrahydroisoquinolin-8-OL

Product 1

HCID 71811404(rac)-4-(8-Hydroxy-5,6,7,8-tetrahydroisoquinolin-4-yl)benzonitrileYield 83%

Procedure

In analogy to the procedure described for the preparation of example 1, (rac)-4-bromo-5,6,7,8-tetrahydroisoquinolin-8-ol (intermediate A-2) was reacted with 4-cyanophenylboronic acid to give the title compound as light brown powder in 83% yield. MS: 251.1 (M+H+).

Sources & evidence

ORD record
ord-cb1bcf2111fb4e33bfb4df16dd7754ec
Source dataset
uspto-grants-2015_11
Patent number
US09187429B2

Reaction notes

Loading…