3,4-Dihydro-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinolin-2(1H)-one → (S)-3-[5-(2-oxo-1,2,3,4-tetrahydro-quinolin-6-yl)-pyridin-3-yloxy]-pyrrolidine-1-carboxylic acid tert-butyl ester

HRID 1774854Notes

Reaction equation

HRID 1774854 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.[C:21]([O:25][C:26]([N:28]1[CH2:32][CH2:31][C@H:30]([O:33][C:34]2[CH:35]=[N:36][CH:37]=[C:38](Br)[CH:39]=2)[CH2:29]1)=[O:27])([CH3:24])([CH3:23])[CH3:22]>>[C:21]([O:25][C:26]([N:28]1[CH2:32][CH2:31][C@H:30]([O:33][C:34]2[CH:35]=[N:36][CH:37]=[C:38]([C:9]3[CH:10]=[C:11]4[C:16](=[CH:17][CH:18]=3)[NH:15][C:14](=[O:19])[CH2:13][CH2:12]4)[CH:39]=2)[CH2:29]1)=[O:27])([CH3:24])([CH3:22])[CH3:23]

Participants

3

Reactant 2

HCID 591171873,4-Dihydro-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinolin-2(1H)-oneHCID 70099125(S)-3-(5-Bromo-pyridin-3-yloxy)-pyrrolidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 86679196(S)-3-[5-(2-oxo-1,2,3,4-tetrahydro-quinolin-6-yl)-pyridin-3-yloxy]-pyrrolidine-1-carboxylic acid tert-butyl ester

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 (S)-3-(5-bromo-pyridin-3-yloxy)-pyrrolidine-1-carboxylic acid tert-butyl ester (intermediate A-29) to give the title compound as a dark grey amorphous solid. MS: 410.6 (M+H+).

Sources & evidence

ORD record
ord-c12e47e28afa4b34910a8bfced484f9c
Source dataset
uspto-grants-2016_02
Patent number
US09260408B2

Reaction notes

Loading…