4-Chlorophenylboronic acid → (rac)-N-(4-(4-Chlorophenyl)-5,6,7,8-tetrahydroisoquinolin-8-yl)propionamide

HRID 714077Notes

Reaction equation

HRID 714077 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.[Cl:17][C:18]1[CH:23]=[CH:22][C:21](B(O)O)=[CH:20][CH:19]=1>>[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([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:20][CH:19]=1

Participants

3

Reactant 2

HCID 742994-Chlorophenylboronic acidHCID 86685953N-(4-Bromo-5,6,7,8-tetrahydroisoquinolin-8-yl)propionamide

Product 1

HCID 89846264(rac)-N-(4-(4-Chlorophenyl)-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-chlorophenylboronic acid to give the title compound as light yellow foam in 86% yield. MS: 315.5 (M+H+, 1Cl).

Sources & evidence

ORD record
ord-1f2ba1785cbf479798ae51891bb951d2
Source dataset
uspto-grants-2015_11
Patent number
US09187429B2

Reaction notes

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