2-Fluoro-4-(trifluoromethyl)benzeneboronic acid → (+)-(R)-4-(2-Fluoro-4-(trifluoromethyl)phenyl)-5,6,7,8-tetrahydroisoquinolin-8-amine

HRID 714087Notes

Reaction equation

HRID 714087 reaction equation
Br[C:2]1[C:11]2[CH2:10][CH2:9][CH2:8][C@@H:7]([NH2:12])[C:6]=2[CH:5]=[N:4][CH:3]=1.[F:13][C:14]1[CH:19]=[C:18]([C:20]([F:23])([F:22])[F:21])[CH:17]=[CH:16][C:15]=1B(O)O>>[F:13][C:14]1[CH:19]=[C:18]([C:20]([F:21])([F:22])[F:23])[CH:17]=[CH:16][C:15]=1[C:2]1[C:11]2[CH2:10][CH2:9][CH2:8][C@@H:7]([NH2:12])[C:6]=2[CH:5]=[N:4][CH:3]=1

Participants

3

Reactant 2

HCID 164141452-Fluoro-4-(trifluoromethyl)benzeneboronic acidHCID 86679930(R)-4-Bromo-5,6,7,8-tetrahydroisoquinolin-8-amine

Product 1

HCID 71811573(+)-(R)-4-(2-Fluoro-4-(trifluoromethyl)phenyl)-5,6,7,8-tetrahydroisoquinolin-8-amineYield 55%

Procedure

In analogy to the procedure described for the preparation of example 1, (+)-(R)-4-bromo-5,6,7,8-tetrahydroisoquinolin-8-amine (intermediate A-11) was reacted with 2-fluoro-4-(trifluoromethyl)phenylboronic acid to give the title compound as brown viscous oil in 55% yield. MS: 311.1 (M+H+).

Sources & evidence

ORD record
ord-3e33f875f8f84f1186c4b0444f9bf4cf
Source dataset
uspto-grants-2015_11
Patent number
US09187429B2

Reaction notes

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