Pyridine → ethyl 3-tert-butyl-1-(quinolin-6-yl)-1H-pyrazole-5-carboxylate

HRID 1711671Notes

Reaction equation

HRID 1711671 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][C:7](B(O)O)=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.N1C=CC=CC=1.[C:20]([C:24]1[CH:28]=[C:27]([C:29]([O:31][CH2:32][CH3:33])=[O:30])[NH:26][N:25]=1)([CH3:23])([CH3:22])[CH3:21]>C(Cl)Cl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[C:20]([C:24]1[CH:28]=[C:27]([C:29]([O:31][CH2:32][CH3:33])=[O:30])[N:26]([C:7]2[CH:6]=[C:5]3[C:10](=[CH:9][CH:8]=2)[N:1]=[CH:2][CH:3]=[CH:4]3)[N:25]=1)([CH3:23])([CH3:21])[CH3:22]

Participants

6

Reactant 3

HCID 1049PyridineHCID 2743509Ethyl 3-tert-butyl-1H-pyrazole-5-carboxylateHCID 4192671Quinolin-6-ylboronic Acid (contains varying amounts of Anhydride)

Product 1

HCID 67251871ethyl 3-tert-butyl-1-(quinolin-6-yl)-1H-pyrazole-5-carboxylateYield 33%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

Quinolin-6-ylboronic acid (0.34 g, 2.0 mmol) was dissolved in CH2Cl2 (30 mL) and pyridine (1 mL) with MS (activated 4 Å) and stirred at RT for 6 hours. Ethyl 3-tert-butyl-1H-pyrazole-5-carboxylate (0.39 g, 2.0 mmol) and copper(II) acetate (0.36 g, 2.0 mmol) were added and the reaction was stirred at RT for 3 days open to air. The reaction mixture was filtered through a pad of Celite®, the filtrate was concentrated in vacuo and purified by silica gel chromatography to obtain ethyl 3-tert-butyl-1-(quinolin-6-yl)-1H-pyrazole-5-carboxylate (0.21 g, 33% yield). MS (ESI) m/z: 324.0 (M+H+).

Workup

  1. filtrationThe reaction mixture was filtered through a pad of Celite®
  2. concentrationthe filtrate was concentrated in vacuo
  3. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-6deebb3be59649a982b54dea4ad6495b
Source dataset
uspto-grants-2010_09
Patent number
US07790756B2

Reaction notes

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