Methyl 8-chloro-1-cyclopropyl-9-methyl-4-oxo-quinolizine-3-carboxylate → HCID 178497215, compound

HRID 1478355Notes

Reaction equation

HRID 1478355 reaction equation
Cl[C:2]1[CH:3]=[CH:4][N:5]2[C:10]([C:11]=1[CH3:12])=[C:9]([CH:13]1[CH2:15][CH2:14]1)[CH:8]=[C:7]([C:16]([O:18][CH3:19])=[O:17])[C:6]2=[O:20].CC1(C)C(C)(C)OB([C:29]2[CH:30]=[CH:31][C:32]([OH:35])=[N:33][CH:34]=2)O1>>[OH:35][C:32]1[N:33]=[CH:34][C:29]([C:2]2[CH:3]=[CH:4][N:5]3[C:10]([C:11]=2[CH3:12])=[C:9]([CH:13]2[CH2:15][CH2:14]2)[CH:8]=[C:7]([C:16]([O:18][CH3:19])=[O:17])[C:6]3=[O:20])=[CH:30][CH:31]=1

Participants

3

Reactant 2

HCID 86696543Methyl 8-chloro-1-cyclopropyl-9-methyl-4-oxo-quinolizine-3-carboxylateHCID 178431084HCID 178431084, compound

Product 1

HCID 178497215HCID 178497215, compound

Procedure

Methyl 8-(6-hydroxypyridin-3-yl)-1-cyclopropyl-9-methyl-4-oxo-4H-quinolizine-3-carboxylate was prepared according to General Procedure A from methyl 8-chloro-1-cyclopropyl-9-methyl-4-oxo-4H-quinolizine-3-carboxylate (100 mg, 0.34 mmol) and 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-ol (90.8 mg, 0.41 mmol). The precipitate was rinsed with DCM and dried in a vacuum stove to afford quantitatively the title compound as a yellow solid.

Workup

  1. customMethyl 8-(6-hydroxypyridin-3-yl)-1-cyclopropyl-9-methyl-4-oxo-4H-quinolizine-3-carboxylate was prepared
  2. washThe precipitate was rinsed with DCM
  3. customdried in a vacuum stove

Sources & evidence

ORD record
ord-06630ff80cac47408f597bd2a802c9ad
Source dataset
uspto-grants-2016_08
Patent number
US09403818B2

Reaction notes

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