tert-Butyl (2-((5-bromopyridin-3-yl)oxy)ethyl)carbamate → {2-[5-(7-Fluoro-1-methyl-2-oxo-1,2,3,4-tetrahydro-quinolin-6-yl)-pyridin-3-yloxy]-ethyl}-carbamic acid tert-butyl ester

HRID 1774871Notes

Reaction equation

HRID 1774871 reaction equation
[F:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][C:8](=[O:13])[N:9]2[CH3:12])=[CH:4][C:3]=1B1OC(C)(C)C(C)(C)O1.[C:23]([O:27][C:28](=[O:40])[NH:29][CH2:30][CH2:31][O:32][C:33]1[CH:34]=[N:35][CH:36]=[C:37](Br)[CH:38]=1)([CH3:26])([CH3:25])[CH3:24]>>[C:23]([O:27][C:28](=[O:40])[NH:29][CH2:30][CH2:31][O:32][C:33]1[CH:34]=[N:35][CH:36]=[C:37]([C:3]2[CH:4]=[C:5]3[C:10](=[CH:11][C:2]=2[F:1])[N:9]([CH3:12])[C:8](=[O:13])[CH2:7][CH2:6]3)[CH:38]=1)([CH3:26])([CH3:24])[CH3:25]

Participants

3

Reactant 2

HCID 71627051tert-Butyl (2-((5-bromopyridin-3-yl)oxy)ethyl)carbamateHCID 86679131HCID 86679131, compound

Product 1

HCID 86679217{2-[5-(7-Fluoro-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 example 45, 7-fluoro-1-methyl-6-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-3,4-dihydro-1H-quinolin-2-one (intermediate A-22) 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 yellow waxy solid. MS: 416.4 (M+H+).

Sources & evidence

ORD record
ord-bda85015b2e04916bde7648effea6dc7
Source dataset
uspto-grants-2016_02
Patent number
US09260408B2

Reaction notes

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