3-Fluoro-4-trifluoromethyl-phenylboronic acid → (+)-(R)-N-(4-(3-Fluoro-4-(trifluoromethyl)phenyl)-5,6,7,8-tetrahydroisoquinolin-8-yl)acetamide

HRID 714092Notes

Reaction equation

HRID 714092 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]1[CH:18]=[C:19](B(O)O)[CH:20]=[CH:21][C:22]=1[C:23]([F:26])([F:25])[F:24]>>[F:16][C:17]1[CH:18]=[C:19]([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:21][C:22]=1[C:23]([F:24])([F:25])[F:26]

Participants

3

Reactant 2

HCID 177500503-Fluoro-4-trifluoromethyl-phenylboronic acidHCID 86699310(+)-(R)-N-(4-Bromo-5,6,7,8-tetrahydroisoquinolin-8-yl)acetamide

Product 1

HCID 71811568(+)-(R)-N-(4-(3-Fluoro-4-(trifluoromethyl)phenyl)-5,6,7,8-tetrahydroisoquinolin-8-yl)acetamideYield 83%

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 3-fluoro-4-(trifluoromethyl)phenylboronic acid to give the title compound as light grey solid in 83% yield. MS: 353.1 (M+H+).

Sources & evidence

ORD record
ord-a19483a100864936aefd7bf55b23767f
Source dataset
uspto-grants-2015_11
Patent number
US09187429B2

Reaction notes

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