tert-Butyl (2-((5-bromopyridin-3-yl)oxy)ethyl)carbamate → {2-[5-(1-Methyl-2-oxo-1,2,3,4-tetrahydro-quinolin-6-yl)-pyridin-3-yloxy]-ethyl}-carbamic acid tert-butyl ester

HRID 1774804Notes

Reaction equation

HRID 1774804 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].[C:22]([O:26][C:27](=[O:39])[NH:28][CH2:29][CH2:30][O:31][C:32]1[CH:33]=[N:34][CH:35]=[C:36](Br)[CH:37]=1)([CH3:25])([CH3:24])[CH3:23]>>[C:22]([O:26][C:27](=[O:39])[NH:28][CH2:29][CH2:30][O:31][C:32]1[CH:33]=[N:34][CH:35]=[C:36]([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:37]=1)([CH3:25])([CH3:23])[CH3:24]

Participants

3

Reactant 2

HCID 71627051tert-Butyl (2-((5-bromopyridin-3-yl)oxy)ethyl)carbamateHCID 722082331-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydroquinolin-2(1H)-one

Product 1

HCID 71533455{2-[5-(1-Methyl-2-oxo-1,2,3,4-tetrahydro-quinolin-6-yl)-pyridin-3-yloxy]-ethyl}-carbamic acid tert-butyl ester

Procedure

In analogy to the procedure described for the preparation of intermediate A-3 [C], 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 [2-(5-bromo-pyridin-3-yloxy)-ethyl]-carbamic acid tert-butyl ester (intermediate A-7) to give the title compound as a white solid. MS: 398.1 (M+H+).

Sources & evidence

ORD record
ord-df9310632f6547ca82b26be0886da154
Source dataset
uspto-grants-2016_02
Patent number
US09260408B2

Reaction notes

Loading…