Stannane, tributyl(1-ethoxyethenyl)- → HCID 57442334, compound

HRID 2262712Notes

Reaction equation

HRID 2262712 reaction equation
Cl[C:2]1[N:3]=[N:4][C:5]([N:8]2[CH2:13][CH2:12][N:11]([CH2:14][C:15]([N:17]3[CH2:22][CH2:21][N:20]([CH:23]4[CH2:26][CH2:25][CH2:24]4)[CH2:19][CH2:18]3)=[O:16])[CH2:10][CH2:9]2)=[CH:6][CH:7]=1.C([Sn](CCCC)(CCCC)[C:32]([O:34]CC)=[CH2:33])CCC>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH:23]1([N:20]2[CH2:21][CH2:22][N:17]([C:15](=[O:16])[CH2:14][N:11]3[CH2:12][CH2:13][N:8]([C:5]4[N:4]=[N:3][C:2]([C:32](=[O:34])[CH3:33])=[CH:7][CH:6]=4)[CH2:9][CH2:10]3)[CH2:18][CH2:19]2)[CH2:26][CH2:25][CH2:24]1

Participants

5

Reactant 2

HCID 619414Stannane, tributyl(1-ethoxyethenyl)-HCID 57443120HCID 57443120, compound

Product 1

HCID 57442334HCID 57442334, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
120 °C

Procedure

In a sealed tube, dissolve 3-chloro-6-{4-[2-(4-cyclobutylpiperazin-1-yl)-2-oxoethyl]-piperazin-1-yl}pyridazine (150 mg, 0.396 mmol), tributyl-(1-ethoxyvinyl)tin (157 mg 0.435 mmol), and Pd(PPh3)4 (23 mg, 0.020 mmol) in toluene (5 mL). Degas the mixture with N2 and seal the tube. Heat the solution at 120° C. overnight. Cool and filter through Celite. Wash the Celite bed with EtOAc (25 mL). Evaporate the solvent and dissolve the residue in 1N HCl and heat at 50° C. for 2 h. Cool and extract with CH2Cl2 (2×25 mL). Discard the extracts. Basify the aqueous phase with 10 N NaOH and extract with CH2Cl2 (2×25 mL). Combine the organic extracts and wash once with saturated aqueous KF solution (50 mL). Dry the organic extract and evaporate to yield the title compound. 1H NMR (CDCl3) δ 7.89 (d, 1H), 6.90 (d, 1H), 3.85 (t, 4H), 3.64-3.59 (m, 4H), 3.26 (s, 2H), 2.77 (s, 3H), 2.75-2.66 (m, 5H), 2.33-2.30 (m, 4H), 1.91-1.68 (m, 4H), 1.43-1.40 (m, 2H); LC-MS (M+1)387.11.

Workup

  1. customDegas the mixture with N2
  2. customseal the tube
  3. temperatureCool
  4. filtrationfilter through Celite
  5. washWash the Celite bed with EtOAc (25 mL)
  6. customEvaporate the solvent
  7. dissolutiondissolve the residue in 1N HCl
  8. temperatureheat at 50° C. for 2 h
  9. temperatureCool
  10. extractionextract with CH2Cl2 (2×25 mL)
  11. extractionBasify the aqueous phase with 10 N NaOH and extract with CH2Cl2 (2×25 mL)
  12. washCombine the organic extracts and wash once with saturated aqueous KF solution (50 mL)
  13. customDry the
  14. extractionorganic extract
  15. customevaporate

Sources & evidence

ORD record
ord-c6a5fd6e667742058902c2475240144e
Source dataset
uspto-grants-2010_12
Patent number
US07851474B2

Reaction notes

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