8-Chloro-1-methyl-6-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-YL)-3,4-dihydro-1H-quinolin-2-one → (rac)-N-(4-(8-Chloro-1-methyl-2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)-6,7-dihydro-5H-cyclopenta[c]pyridin-7-yl)propionamide

HRID 530362Notes

Reaction equation

HRID 530362 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4](B2OC(C)(C)C(C)(C)O2)[CH:5]=[C:6]2[C:11]=1[N:10]([CH3:12])[C:9](=[O:13])[CH2:8][CH2:7]2.Br[C:24]1[C:25]2[CH2:32][CH2:31][CH:30]([NH:33][C:34](=[O:37])[CH2:35][CH3:36])[C:26]=2[CH:27]=[N:28][CH:29]=1>>[Cl:1][C:2]1[CH:3]=[C:4]([C:24]2[C:25]3[CH2:32][CH2:31][CH:30]([NH:33][C:34](=[O:37])[CH2:35][CH3:36])[C:26]=3[CH:27]=[N:28][CH:29]=2)[CH:5]=[C:6]2[C:11]=1[N:10]([CH3:12])[C:9](=[O:13])[CH2:8][CH2:7]2

Participants

3

Reactant 2

HCID 722080468-Chloro-1-methyl-6-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-YL)-3,4-dihydro-1H-quinolin-2-oneHCID 86685956N-(4-Bromo-6,7-dihydro-5H-cyclopenta[c]pyridin-7-yl)propionamide

Product 1

HCID 71538466(rac)-N-(4-(8-Chloro-1-methyl-2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)-6,7-dihydro-5H-cyclopenta[c]pyridin-7-yl)propionamideYield 65%

Procedure

In analogy to the procedure described for the preparation of example 28, 8-chloro-1-methyl-6-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-3,4-dihydro-1H-quinolin-2-one (intermediate A-8) and (rac)-N-(4-bromo-6,7-dihydro-5H-cyclopenta[c]pyridin-7-yl)propionamide (intermediate A-3) were used to give the title compound as a white powder in 65% yield. MS: 384.3 (M+H)+.

Sources & evidence

ORD record
ord-b6d164fdccd141ba87f5e23ec4cdd472
Source dataset
uspto-grants-2016_05
Patent number
US09353081B2

Reaction notes

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