HCID 86679131, compound → (rac)-N-(4-(7-Fluoro-1-methyl-2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)-6,7-dihydro-5H-cyclopenta[c]pyridin-7-yl)propionamide

HRID 530355Notes

Reaction equation

HRID 530355 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.[F:16][C:17]1[CH:26]=[C:25]2[C:20]([CH2:21][CH2:22][C:23](=[O:28])[N:24]2[CH3:27])=[CH:19][C:18]=1B1OC(C)(C)C(C)(C)O1>>[F:16][C:17]1[CH:26]=[C:25]2[C:20]([CH2:21][CH2:22][C:23](=[O:28])[N:24]2[CH3:27])=[CH:19][C:18]=1[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

Participants

3

Reactant 2

HCID 86679131HCID 86679131, compoundHCID 86685956N-(4-Bromo-6,7-dihydro-5H-cyclopenta[c]pyridin-7-yl)propionamide

Product 1

HCID 71536765(rac)-N-(4-(7-Fluoro-1-methyl-2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)-6,7-dihydro-5H-cyclopenta[c]pyridin-7-yl)propionamideYield 72%

Procedure

In analogy to the procedure described for the preparation of intermediate A-2 [E], (rac)-N-(4-bromo-6,7-dihydro-5H-cyclopenta[c]pyridin-7-yl)propionamide (intermediate A-3) was reacted with 7-fluoro-1-methyl-6-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-3,4-dihydro-1H-quinolin-2-one (intermediate A-9) to give the title compound as a light brown solid in 72% yield. MS: 368.2 (M+H+).

Sources & evidence

ORD record
ord-42cc6b5adcb54b6f888054bed44258a9
Source dataset
uspto-grants-2016_05
Patent number
US09353081B2

Reaction notes

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