4-Chloro-3-fluorophenylboronic Acid → (rac)-N-(4-(4-Chloro-3-fluorophenyl)-6,7-dihydro-5H-cyclopenta[c]pyridin-7-yl)propionamide

HRID 714082Notes

Reaction equation

HRID 714082 reaction equation
Br[C:2]1[C:3]2[CH2:10][CH2:9][CH:8]([NH:11][C:12](=[O:15])[CH2:13][CH3:14])[C:4]=2[CH:5]=[N:6][CH:7]=1.[Cl:16][C:17]1[CH:22]=[CH:21][C:20](B(O)O)=[CH:19][C:18]=1[F:26]>>[Cl:16][C:17]1[CH:22]=[CH:21][C:20]([C:2]2[C:3]3[CH2:10][CH2:9][CH:8]([NH:11][C:12](=[O:15])[CH2:13][CH3:14])[C:4]=3[CH:5]=[N:6][CH:7]=2)=[CH:19][C:18]=1[F:26]

Participants

3

Reactant 2

HCID 27786564-Chloro-3-fluorophenylboronic AcidHCID 86685956N-(4-Bromo-6,7-dihydro-5H-cyclopenta[c]pyridin-7-yl)propionamide

Product 1

HCID 71811646(rac)-N-(4-(4-Chloro-3-fluorophenyl)-6,7-dihydro-5H-cyclopenta[c]pyridin-7-yl)propionamideYield 87%

Procedure

In analogy to the procedure described for the preparation of example 1, (rac)-N-(4-bromo-6,7-dihydro-5H-cyclopenta[c]pyridin-7-yl)propionamide (intermediate A-4) was reacted with 4-chloro-3-fluorophenylboronic acid to give the title compound as grey solid in 87% yield. MS: 319.1 (M+H+, 1Cl).

Sources & evidence

ORD record
ord-1cee0e26c8b6416ea5675a7c04c13870
Source dataset
uspto-grants-2015_11
Patent number
US09187429B2

Reaction notes

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