Methyl 8-chloro-1-cyclopropyl-9-methyl-4-oxo-quinolizine-3-carboxylate → HCID 178497213, compound

HRID 1478370Notes

Reaction equation

HRID 1478370 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].[CH:21]1([C:24]2[C:32]3[C:27](=[CH:28][CH:29]=[C:30](B4OC(C)(C)C(C)(C)O4)[CH:31]=3)[N:26](C(OC(C)(C)C)=O)[N:25]=2)[CH2:23][CH2:22]1>>[CH:21]1([C:24]2[C:32]3[C:27](=[CH:28][CH:29]=[C:30]([C:2]4[CH:3]=[CH:4][N:5]5[C:10]([C:11]=4[CH3:12])=[C:9]([CH:13]4[CH2:15][CH2:14]4)[CH:8]=[C:7]([C:16]([O:18][CH3:19])=[O:17])[C:6]5=[O:20])[CH:31]=3)[NH:26][N:25]=2)[CH2:23][CH2:22]1

Participants

3

Reactant 2

HCID 86696543Methyl 8-chloro-1-cyclopropyl-9-methyl-4-oxo-quinolizine-3-carboxylateHCID 86696764HCID 86696764, compound

Product 1

HCID 178497213HCID 178497213, compoundYield 78.1%

Procedure

Methyl 8-(3-cyclopropyl-1H-indazol-5-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 (75 mg, 0.26 mmol) and tert-butyl 3-cyclopropyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole-1-carboxylate (157.9 mg, 0.41 mmol). Purification by flash silica column chromatography (DCM:MeOH) (1:0 to 9:1) afforded the title compound as a yellow solid (84 mg, 60%).

Workup

  1. customMethyl 8-(3-cyclopropyl-1H-indazol-5-yl)-1-cyclopropyl-9-methyl-4-oxo-4H-quinolizine-3-carboxylate was prepared
  2. customPurification by flash silica column chromatography (DCM:MeOH) (1:0 to 9:1)

Sources & evidence

ORD record
ord-1c2fcf291d5b48a2af4c50415a0dd30b
Source dataset
uspto-grants-2016_08
Patent number
US09403818B2

Reaction notes

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