Pyridine → ethyl 1-(1-(4-methoxybenzyl)-2-oxo-1,2-dihydroquinolin-6-yl)-3-t-butyl-1H-pyrazole-5-carboxylate

HRID 1696542Notes

Reaction equation

HRID 1696542 reaction equation
[CH3:1][O:2][C:3]1[CH:23]=[CH:22][C:6]([CH2:7][N:8]2[C:17]3[C:12](=[CH:13][C:14](B(O)O)=[CH:15][CH:16]=3)[CH:11]=[CH:10][C:9]2=[O:21])=[CH:5][CH:4]=1.N1C=CC=CC=1.[C:30]([C:34]1[CH:38]=[C:37]([C:39]([O:41][CH2:42][CH3:43])=[O:40])[NH:36][N:35]=1)([CH3:33])([CH3:32])[CH3:31].B(O)O>C(Cl)Cl.CC([O-])=O.CC([O-])=O.[Cu+2]>[CH3:1][O:2][C:3]1[CH:23]=[CH:22][C:6]([CH2:7][N:8]2[C:17]3[C:12](=[CH:13][C:14]([N:36]4[C:37]([C:39]([O:41][CH2:42][CH3:43])=[O:40])=[CH:38][C:34]([C:30]([CH3:31])([CH3:33])[CH3:32])=[N:35]4)=[CH:15][CH:16]=3)[CH:11]=[CH:10][C:9]2=[O:21])=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 1049PyridineHCID 61668Boronic AcidHCID 2743509Ethyl 3-tert-butyl-1H-pyrazole-5-carboxylateHCID 672721411-(4-Methoxybenzyl)-2-oxo-1,2-dihydroquinolin-6-ylboronic acid

Product 1

HCID 67271613ethyl 1-(1-(4-methoxybenzyl)-2-oxo-1,2-dihydroquinolin-6-yl)-3-t-butyl-1H-pyrazole-5-carboxylateYield 94%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

1-(4-Methoxybenzyl)-2-oxo-1,2-dihydroquinolin-6-ylboronic acid (1.8 g, 5.8 mmol) was dissolved in CH2Cl2 (120 mL) and pyridine (10 mL) with molecular sieves (activated, 4 A) and the solution was kept overnight at RT. Commercially available ethyl 3-t-butyl-1H-pyrazole-5-carboxylate (1.2 g, 5.8 mmol), Cu(OAc)2 (1.1 g, 5.8 mmol) and molecular sieves (4 Å activated, powder) were added to the boronic acid solution and the reaction mixture was stirred open to the air at RT for 3 days. The reaction mixture was filtered through a pad of Celite®, and the filtrate was evaporated under reduced pressureand purified by silica gel column chromatography to yield ethyl 1-(1-(4-methoxybenzyl)-2-oxo-1,2-dihydroquinolin-6-yl)-3-t-butyl-1H-pyrazole-5-carboxylate (2.5 g, 94% yield). LC-MS (EI) m/z: 460.3 (M+H+).

Workup

  1. filtrationThe reaction mixture was filtered through a pad of Celite®
  2. customthe filtrate was evaporated
  3. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-dcb4a2d1ab5e479aa40c53e7658c298a
Source dataset
uspto-grants-2012_04
Patent number
US08163756B2

Reaction notes

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