4-Trifluoromethyl-6-cyclopropylphenylboronic acid pinacol ester → (R)-N-(4-(2-Cyclopropyl-4-(trifluoromethyl)phenyl)-5,6,7,8-tetrahydroisoquinolin-8-yl)propionamide

HRID 714113Notes

Reaction equation

HRID 714113 reaction equation
Br[C:2]1[C:11]2[CH2:10][CH2:9][CH2:8][C@@H: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:38])([F:37])[C:19]1[CH:24]=[C:23]([CH:25]2[CH2:27][CH2:26]2)[C:22](B2OC(C)(C)C(C)(C)O2)=[CH:21][CH:20]=1>>[CH:25]1([C:23]2[CH:24]=[C:19]([C:18]([F:17])([F:37])[F:38])[CH:20]=[CH:21][C:22]=2[C:2]2[C:11]3[CH2:10][CH2:9][CH2:8][C@@H:7]([NH:12][C:13](=[O:16])[CH2:14][CH3:15])[C:6]=3[CH:5]=[N:4][CH:3]=2)[CH2:26][CH2:27]1

Participants

3

Reactant 2

HCID 665212824-Trifluoromethyl-6-cyclopropylphenylboronic acid pinacol esterHCID 86699312(R)-N-(4-Bromo-5,6,7,8-tetrahydroisoquinolin-8-yl)propionamide

Product 1

HCID 71811448(R)-N-(4-(2-Cyclopropyl-4-(trifluoromethyl)phenyl)-5,6,7,8-tetrahydroisoquinolin-8-yl)propionamideYield 84%

Procedure

In analogy to the procedure described for the preparation of example 1, (R)—N-(4-bromo-5,6,7,8-tetrahydroisoquinolin-8-yl)propionamide (intermediate A-16) was reacted with 4-trifluoromethyl-6-cyclopropylphenylboronic acid pinacol ester acid to give the title compound as colorless oil in 84% yield. MS: 389.2 (M+H+).

Sources & evidence

ORD record
ord-daf3b7e28c684616a4734ced5f5c8f87
Source dataset
uspto-grants-2015_11
Patent number
US09187429B2

Reaction notes

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