3-[2-(2-Oxocyclohexyl)-3-oxo-2,3-dihydropyridazin-6-yl]-2-phenylpyrazolo[1,5-a]pyridine → 3-[2-(2-Methylenecyclohexyl)-3-oxo-2,3-dihydropyridazin-6-yl]-2-phenylpyrazolo[1,5-a]pyridine

HRID 276949Notes

Reaction equation

HRID 276949 reaction equation
[CH3:1]C(C)([O-])C.[K+].O=[C:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[N:14]1[C:19](=[O:20])[CH:18]=[CH:17][C:16]([C:21]2[C:22]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[N:23][N:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=23)=[N:15]1>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O1CCCC1>[CH2:1]=[C:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[N:14]1[C:19](=[O:20])[CH:18]=[CH:17][C:16]([C:21]2[C:22]([C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=3)=[N:23][N:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=23)=[N:15]1

Participants

5

Reactant 2

HCID 110690413-[2-(2-Oxocyclohexyl)-3-oxo-2,3-dihydropyridazin-6-yl]-2-phenylpyrazolo[1,5-a]pyridineHCID 23665647Potassium tert-butoxide

Product 1

HCID 226292583-[2-(2-Methylenecyclohexyl)-3-oxo-2,3-dihydropyridazin-6-yl]-2-phenylpyrazolo[1,5-a]pyridineYield 37.4%

Reagents, catalysts & solvents 2

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
2.5 °C

Procedure

To a stirred suspension of methyltriphenylphosphonium bromide (1.39 g) in tetrahydrofuran (30 ml) was added potassium tert-butoxide (437 mg) under nitrogen atmosphere at 0° C. After the mixture was stirred at 0-5° C. for 1.5 hours, to this was added a solution of 3-[2-(2-oxocyclohexyl)-3-oxo-2,3-dihydropyridazin-6-yl]-2-phenylpyrazolo[1,5-a]pyridine (500 mg) in tetrahydrofuran (10 ml). The mixture was stirred at room temperature for 4 hours and stood at room temperature overnight. Insoluble materials were filtered off and the filtrate was evaporated in vacuo. The residue was dissolved in dichloromethane (30 ml). The dichloromethane solution was washed with brine (20 ml), dried over anhydrous sodium sulfate, and evaporated in vacuo. The crude material was purified by column chromatography on silica gel using dichloromethane as an eluant to give colorless crystals of 3-[2-(2-methylenecyclohexyl)-3-oxo-2,3-dihydropyridazin-6-yl]-2-phenylpyrazolo[1,5-a]pyridine (186 mg).

Workup

  1. stirringThe mixture was stirred at room temperature for 4 hours
  2. waitstood at room temperature overnight
  3. filtrationInsoluble materials were filtered off
  4. customthe filtrate was evaporated in vacuo
  5. dissolutionThe residue was dissolved in dichloromethane (30 ml)
  6. washThe dichloromethane solution was washed with brine (20 ml)
  7. dry with materialdried over anhydrous sodium sulfate
  8. customevaporated in vacuo
  9. customThe crude material was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-2cc7c4ee1eda4e368bb71ce80562078b
Source dataset
uspto-grants-2002_03
Patent number
US06355640B1

Reaction notes

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