6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydro-1H-isoindol-1-one → methyl 8-(3-oxoisoindolin-5-yl)-1-cyclopropyl-9-methyl-4-oxo-4H-quinolizine-3-carboxylate

HRID 1478367Notes

Reaction equation

HRID 1478367 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:37]=[C:36]3[C:32]([CH2:33][NH:34][C:35]3=[O:38])=[CH:31][CH:30]=2)O1>>[O:38]=[C:35]1[C:36]2[C:32](=[CH:31][CH:30]=[C:29]([C:2]3[CH:3]=[CH:4][N:5]4[C:10]([C:11]=3[CH3:12])=[C:9]([CH:13]3[CH2:15][CH2:14]3)[CH:8]=[C:7]([C:16]([O:18][CH3:19])=[O:17])[C:6]4=[O:20])[CH:37]=2)[CH2:33][NH:34]1

Participants

3

Reactant 2

HCID 468564156-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydro-1H-isoindol-1-oneHCID 86696543Methyl 8-chloro-1-cyclopropyl-9-methyl-4-oxo-quinolizine-3-carboxylate

Product 1

HCID 86696760methyl 8-(3-oxoisoindolin-5-yl)-1-cyclopropyl-9-methyl-4-oxo-4H-quinolizine-3-carboxylateYield 87.8%

Procedure

Methyl 8-(3-oxoisoindolin-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 (100 mg, 0.34 mmol) and 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)isoindolin-1-one (106.5 mg, 0.41 mmol). The precipitate was rinsed with DCM and dried in a vacuum stove to afford the title compound as a yellow solid (116 mg, 87%).

Workup

  1. customMethyl 8-(3-oxoisoindolin-5-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-117228daa7ab4ecc982a97bb47a983f9
Source dataset
uspto-grants-2016_08
Patent number
US09403818B2

Reaction notes

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