(4-Fluoro-3-methylphenyl)boronic acid → (rac)-N-(4-(4-Fluoro-3-methylphenyl)-5,6,7,8-tetrahydroisoquinolin-8-yl)propionamide

HRID 714078Notes

Reaction equation

HRID 714078 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.[F:17][C:18]1[CH:23]=[CH:22][C:21](B(O)O)=[CH:20][C:19]=1[CH3:27]>>[F: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][C:19]=1[CH3:27]

Participants

3

Reactant 2

HCID 2774580(4-Fluoro-3-methylphenyl)boronic acidHCID 86685953N-(4-Bromo-5,6,7,8-tetrahydroisoquinolin-8-yl)propionamide

Product 1

HCID 89846252(rac)-N-(4-(4-Fluoro-3-methylphenyl)-5,6,7,8-tetrahydroisoquinolin-8-yl)propionamideYield 82%

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-fluoro-3-methylphenylboronic acid to give the title compound as light yellow foam in 82% yield. MS: 313.5 (M+H+).

Sources & evidence

ORD record
ord-e4c36c3737ff4aad934591b72f4e3bb0
Source dataset
uspto-grants-2015_11
Patent number
US09187429B2

Reaction notes

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