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

HRID 714076Notes

Reaction equation

HRID 714076 reaction equation
Br[C:2]1[C:11]2[CH2:10][CH2:9][CH2:8][CH:7]([NH:12][C:13](=[O:16])[CH2:14][CH3:15])[C:6]=2[CH:5]=[N:4][CH:3]=1.[F:17][C:18]([F:29])([F:28])[C:19]1[CH:24]=[CH:23][C:22](B(O)O)=[CH:21][CH:20]=1>>[F:17][C:18]([F:29])([F:28])[C:19]1[CH:24]=[CH:23][C:22]([C:2]2[C:11]3[CH2:10][CH2:9][CH2:8][CH:7]([NH:12][C:13](=[O:16])[CH2:14][CH3:15])[C:6]=3[CH:5]=[N:4][CH:3]=2)=[CH:21][CH:20]=1

Participants

3

Reactant 2

HCID 27343894-(Trifluoromethyl)phenylboronic acidHCID 86685953N-(4-Bromo-5,6,7,8-tetrahydroisoquinolin-8-yl)propionamide

Product 1

HCID 71811410(rac)-N-(4-(4-(Trifluoromethyl)phenyl)-5,6,7,8-tetrahydroisoquinolin-8-yl)propionamideYield 86%

Procedure

In analogy to the procedure described for the preparation of example 1, (rac)-N-(4-bromo-5,6,7,8-tetrahydroisoquinolin-8-yl)propionamide (intermediate A-1) was reacted with 4-(trifluoromethyl)phenylboronic acid to give the title compound as light grey foam in 86% yield. MS: 349.2 (M+H+).

Sources & evidence

ORD record
ord-59be2bfbecec4b23bb557d8231c1db61
Source dataset
uspto-grants-2015_11
Patent number
US09187429B2

Reaction notes

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