3,4-Dihydro-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinolin-2(1H)-one → 3-Chloro-pyridine-2-carboxylic acid methyl-[5-(2-oxo-1,2,3,4-tetrahydro-quinolin-6-yl)-pyridin-3-ylmethyl]-amide

HRID 1774855Notes

Reaction equation

HRID 1774855 reaction equation
CC1(C)C(C)(C)OB([C:9]2[CH:10]=[C:11]3[C:16](=[CH:17][CH:18]=2)[NH:15][C:14](=[O:19])[CH2:13][CH2:12]3)O1.Br[C:22]1[CH:23]=[C:24]([CH2:28][N:29]([CH3:39])[C:30](=[O:38])[C:31]2[C:36]([Cl:37])=[CH:35][CH:34]=[CH:33][N:32]=2)[CH:25]=[N:26][CH:27]=1>>[CH3:39][N:29]([CH2:28][C:24]1[CH:25]=[N:26][CH:27]=[C:22]([C:9]2[CH:10]=[C:11]3[C:16](=[CH:17][CH:18]=2)[NH:15][C:14](=[O:19])[CH2:13][CH2:12]3)[CH:23]=1)[C:30]([C:31]1[C:36]([Cl:37])=[CH:35][CH:34]=[CH:33][N:32]=1)=[O:38]

Participants

3

Reactant 2

HCID 591171873,4-Dihydro-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinolin-2(1H)-oneHCID 86679148N-((5-Bromopyridin-3-yl)methyl)-3-chloro-N-methylpicolinamide

Product 1

HCID 866791973-Chloro-pyridine-2-carboxylic acid methyl-[5-(2-oxo-1,2,3,4-tetrahydro-quinolin-6-yl)-pyridin-3-ylmethyl]-amide

Procedure

In analogy to the procedure described for the preparation of example 45, 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydroquinolin-2(1H)-one (intermediate A-34) has been coupled to N-((5-bromopyridin-3-yl)methyl)-3-chloro-N-methylpicolinamide (intermediate A-57) to give the title compound as a light brown amorphous solid. MS: 407.5 (M+H+).

Sources & evidence

ORD record
ord-902b0a37aafa42ebbc2e19c63a5b9138
Source dataset
uspto-grants-2016_02
Patent number
US09260408B2

Reaction notes

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