HCID 68297022, compound → HCID 86696761, compound

HRID 1478368Notes

Reaction equation

HRID 1478368 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].[CH3:21][NH:22][C:23]1[CH:28]=[CH:27][C:26](B2OC(C)(C)C(C)(C)O2)=[CH:25][C:24]=1[CH3:38]>>[CH3:38][C:24]1[CH:25]=[C:26]([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:27]=[CH:28][C:23]=1[NH:22][CH3:21]

Participants

3

Reactant 2

HCID 68297022HCID 68297022, compoundHCID 86696543Methyl 8-chloro-1-cyclopropyl-9-methyl-4-oxo-quinolizine-3-carboxylate

Product 1

HCID 86696761HCID 86696761, compoundYield 39.1%

Procedure

Methyl 8-(3-methyl-4-(methylamino)phenyl)-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 N,2-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (101.5 mg, 0.41 mmol). The residue was rinsed with DCM and dried in a vacuum stove to afford the title compound as a yellow solid (50 mg, 39%).

Workup

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

Sources & evidence

ORD record
ord-e1111925bc3441d28ac31cbb5aef26ca
Source dataset
uspto-grants-2016_08
Patent number
US09403818B2

Reaction notes

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