4-Cyanophenylboronic acid → (+)-(R)-N-(4-(4-Cyanophenyl)-5,6,7,8-tetrahydroisoquinolin-8-yl)acetamide

HRID 714091Notes

Reaction equation

HRID 714091 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.[C:16]([C:18]1[CH:23]=[CH:22][C:21](B(O)O)=[CH:20][CH:19]=1)#[N:17]>>[C:16]([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)#[N:17]

Participants

3

Reactant 2

HCID 27343264-Cyanophenylboronic acidHCID 86699310(+)-(R)-N-(4-Bromo-5,6,7,8-tetrahydroisoquinolin-8-yl)acetamide

Product 1

HCID 71811570(+)-(R)-N-(4-(4-Cyanophenyl)-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-cyanophenylboronic acid to give the title compound as off-white solid in 87% yield. MS: 292.1 (M+H+).

Sources & evidence

ORD record
ord-00d9659774b2476a9a53087c2eb6eb3c
Source dataset
uspto-grants-2015_11
Patent number
US09187429B2

Reaction notes

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