3-Chloro-4-fluorophenylboronic Acid (contains varying amounts of Anhydride) → (rac)-N-(4-(3-Chloro-4-fluorophenyl)-5,6,7,8-tetrahydroisoquinolin-8-yl)propionamide

HRID 714075Notes

Reaction equation

HRID 714075 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:19]=[C:20](B(O)O)[CH:21]=[CH:22][C:23]=1[F:24]>>[Cl:17][C:18]1[CH:19]=[C:20]([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:21]=[CH:22][C:23]=1[F:24]

Participants

3

Reactant 2

HCID 27346603-Chloro-4-fluorophenylboronic Acid (contains varying amounts of Anhydride)HCID 86685953N-(4-Bromo-5,6,7,8-tetrahydroisoquinolin-8-yl)propionamide

Product 1

HCID 71811409(rac)-N-(4-(3-Chloro-4-fluorophenyl)-5,6,7,8-tetrahydroisoquinolin-8-yl)propionamideYield 74%

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 3-chloro-4-fluorophenylboronic acid to give the title compound as light grey foam in 74% yield. MS: 333.1 (M+H+, 1Cl).

Sources & evidence

ORD record
ord-c18eef64617948bf8c2e7c79f11c1e68
Source dataset
uspto-grants-2015_11
Patent number
US09187429B2

Reaction notes

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