1-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydroquinolin-2(1H)-one → (R)-2-Methyl-propane-2-sulfinic acid [4-chloro-5-(1-methyl-2-oxo-1,2,3,4-tetrahydro-quinolin-6-yl)-pyridin-3-ylmethyl]-amide

HRID 1774857Notes

Reaction equation

HRID 1774857 reaction equation
[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][C:8](B3OC(C)(C)C(C)(C)O3)=[CH:9][CH:10]=2)[CH2:5][CH2:4][C:3]1=[O:21].Br[C:23]1[C:24]([Cl:37])=[C:25]([CH2:29][NH:30][S@@:31]([C:33]([CH3:36])([CH3:35])[CH3:34])=[O:32])[CH:26]=[N:27][CH:28]=1>>[Cl:37][C:24]1[C:23]([C:8]2[CH:7]=[C:6]3[C:11](=[CH:10][CH:9]=2)[N:2]([CH3:1])[C:3](=[O:21])[CH2:4][CH2:5]3)=[CH:28][N:27]=[CH:26][C:25]=1[CH2:29][NH:30][S@@:31]([C:33]([CH3:36])([CH3:35])[CH3:34])=[O:32]

Participants

3

Reactant 2

HCID 722082331-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydroquinolin-2(1H)-oneHCID 86679149(R)-N-((5-Bromo-4-chloropyridin-3-yl)methyl)-2-methylpropane-2-sulfinamide

Product 1

HCID 86679199(R)-2-Methyl-propane-2-sulfinic acid [4-chloro-5-(1-methyl-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, 1-methyl-6-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-3,4-dihydro-1H-quinolin-2-one (intermediate A-1) has been coupled to (R)—N-((5-bromo-4-chloropyridin-3-yl)methyl)-2-methylpropane-2-sulfinamide (intermediate A-58) to give the title compound as an orange solid. MS: 406.4 (M+H+).

Sources & evidence

ORD record
ord-3ffdbfe648144fc784bc105ed179d9f9
Source dataset
uspto-grants-2016_02
Patent number
US09260408B2

Reaction notes

Loading…