4-(Trifluoromethyl)phenylboronic acid → (+)-(R)-N-(4-(4-(Trifluoromethyl)phenyl)-5,6,7,8-tetrahydroisoquinolin-8-yl)acetamide

HRID 714090Notes

Reaction equation

HRID 714090 reaction equation
Br[C:2]1[C:11]2[CH2:10][CH2:9][CH2:8][C@@H:7]([NH:12][C:13](=[O:15])[CH3:14])[C:6]=2[CH:5]=[N:4][CH:3]=1.[F:16][C:17]([F:28])([F:27])[C:18]1[CH:23]=[CH:22][C:21](B(O)O)=[CH:20][CH:19]=1>>[F:16][C:17]([F:28])([F:27])[C:18]1[CH:23]=[CH:22][C:21]([C:2]2[C:11]3[CH2:10][CH2:9][CH2:8][C@@H:7]([NH:12][C:13](=[O:15])[CH3:14])[C:6]=3[CH:5]=[N:4][CH:3]=2)=[CH:20][CH:19]=1

Participants

3

Reactant 2

HCID 27343894-(Trifluoromethyl)phenylboronic acidHCID 86699310(+)-(R)-N-(4-Bromo-5,6,7,8-tetrahydroisoquinolin-8-yl)acetamide

Product 1

HCID 71811569(+)-(R)-N-(4-(4-(Trifluoromethyl)phenyl)-5,6,7,8-tetrahydroisoquinolin-8-yl)acetamideYield 87%

Procedure

In analogy to the procedure described for the preparation of example 1, (+)-(R)—N-(4-bromo-5,6,7,8-tetrahydroisoquinolin-8-yl)acetamide (intermediate A-12) was reacted with 4-(trifluoromethyl)phenylboronic acid to give the title compound as white solid in 87% yield. MS: 335.1 (M+H+).

Sources & evidence

ORD record
ord-58a718812e404607baf9b8842f0a7458
Source dataset
uspto-grants-2015_11
Patent number
US09187429B2

Reaction notes

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