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Pyridine → ethyl 3-methyl-1-(6-methoxy-2-naphthyl)-1H-pyrazole-5-carboxylate

HRID 2119440
Notes
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Reaction equation

HRID 2119440 reaction equation
B(O)O.[CH3:4][C:5]1[CH:9]=[C:8]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[NH:7][N:6]=1.[N:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C(Cl)Cl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[CH3:4][C:5]1[CH:9]=[C:8]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[N:7]([C:16]2[CH:4]=[CH:5][C:9]3[C:18](=[CH:19][CH:20]=[C:10]([O:12][CH3:13])[CH:8]=3)[CH:17]=2)[N:6]=1.[CH3:4][C:5]1[N:15]([C:20]2[CH:4]=[CH:5][C:9]3[C:18](=[CH:17][CH:16]=[C:10]([O:12][CH3:13])[CH:8]=3)[CH:19]=2)[N:7]=[C:8]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:9]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 1049PyridineHCID 61668Boronic AcidHCID 178469061HCID 178469061, compound

Product 2

HCID 22728868ethyl 3-methyl-1-(6-methoxy-2-naphthyl)-1H-pyrazole-5-carboxylateYield 37%HCID 22728899ethyl 5-methyl-1-(6-methoxy-2-naphthyl)-1H-pyrazole-3-carboxylateYield 25%

Reagents, catalysts & solvents

2
HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of the above-prepared boronic acid (0.84 g, 3.2 mmol) and ethyl 3-methylpyrazole-5-carboxylate (0.49 g, 3.2 mmol) in 20 mL dry DCM were added pyridine (0.77 mL, 9.5 mmol) and anhydrous powder of copper(II) acetate (1.15 g, 6.3 mmol). Some activated molecular sieve powder was added afterwards. The resulting slurry was stirred for 4 days under argon. The mixture was diluted with DCM. It was filtered through celite. The blue filtrate was washed with water (×2), dried, concentrated and purified by flash column to separately afford ethyl 3-methyl-1-(6-methoxy-2-naphthyl)-1H-pyrazole-5-carboxylate [37% yield. Rf 0.80 (1:1 EtOAc:hexane). ES-MS: (M+H)+ 311] and ethyl 5-methyl-1-(6-methoxy-2-naphthyl)-1H-pyrazole-3-carboxylate [25% yield. Rf 0.69 (1:1 EtOAc:hexane). ES-MS: (M+H)+ 311] in a 1.5:1 ratio.

Workup

  1. additionSome activated molecular sieve powder was added afterwards
  2. filtrationIt was filtered through celite
  3. washThe blue filtrate was washed with water (×2)
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-30d7955ef2ec48068168f5cf0865451e
Source dataset
uspto-grants-2004_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06686368B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes