4-(Trifluoromethyl)phenylboronic acid → (rac)-4-(4-(Trifluoromethyl)phenyl)-5,6,7,8-tetrahydroisoquinolin-8-ol

HRID 714112Notes

Reaction equation

HRID 714112 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.[F:13][C:14]([F:25])([F:24])[C:15]1[CH:20]=[CH:19][C:18](B(O)O)=[CH:17][CH:16]=1>>[F:13][C:14]([F:25])([F:24])[C:15]1[CH:20]=[CH:19][C:18]([C:2]2[C:11]3[CH2:10][CH2:9][CH2:8][CH:7]([OH:12])[C:6]=3[CH:5]=[N:4][CH:3]=2)=[CH:17][CH:16]=1

Participants

3

Reactant 2

HCID 27343894-(Trifluoromethyl)phenylboronic acidHCID 717438914-Bromo-5,6,7,8-tetrahydroisoquinolin-8-OL

Product 1

HCID 71811450(rac)-4-(4-(Trifluoromethyl)phenyl)-5,6,7,8-tetrahydroisoquinolin-8-olYield 86%

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-(trifluoromethyl)phenylboronic acid to give the title compound as white solid in 86% yield. MS: 294.1 (M+H+).

Sources & evidence

ORD record
ord-2e0647af60c348c7806b27948af4a4b5
Source dataset
uspto-grants-2015_11
Patent number
US09187429B2

Reaction notes

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