Acetonitrile → HCID 69487094, compound

HRID 498239

Reaction equation

HRID 498239 reaction equation
CO[C:3](=[O:16])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]2[N:11]=[N:12][CH:13]=[CH:14][CH:15]=2)[CH:5]=1.[C:17]([C:20]1C=C(B(O)O)C=CC=1)([OH:19])=[O:18].ClC1N=N[CH:33]=[CH:34][CH:35]=1.O=S(Cl)Cl.[C:40](#N)C>C([O-])([O-])=O.[Na+].[Na+].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>[C:34]([O:19][C:17](=[O:18])[CH2:20][C:3](=[O:16])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]2[N:11]=[N:12][CH:13]=[CH:14][CH:15]=2)[CH:5]=1)([CH3:33])([CH3:35])[CH3:40]

Participants

8

Reactant 5

HCID 6342AcetonitrileHCID 24386Thionyl ChlorideHCID 27339573-Carboxyphenylboronic acidHCID 112749893-ChloropyridazineHCID 694896873-Pyridazin-3-yl-benzoic acid methyl ester

Product 1

HCID 69487094HCID 69487094, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 10340Sodium CarbonateSolvent

Procedure

The title compound was prepared from 3-pyridazin-3-yl-benzoic acid methyl ester [prepared by the following procedure: A mixture of 3-carboxyphenylboronic acid (6.98 g, 42.06 mmol) and 3-chloropyridazine [CAS-No. 1120-95-2] (4.817 g, 42.06 mmol) in acetonitrile (210 ml) and 0.4M Na2CO3-solution (210 ml) was degassed and Pd(Ph3P)4 (2.43 g, 2.1 mmol) was added. The reaction mixture was refluxed for 15 h and evaporated to dryness [Synlett 2000 (6), 829-831]. The residue was suspended in MeOH (500 ml), SOCl2 (15.3 ml, 211 mmol) was added dropwise at 23° C. and the reaction mixture was stirred at reflux for 16 h. Concentrated in vacuum to about 100 mL, diluted with EtOAc, washed with sat. NaHCO3-solution and brine, dried over Na2SO4. Removal of the solvent in vacuum left a brown residue, which was purified by silica gel column chromatography with cyclohexane/EtOAc.] (7.35 g, 34.32 mmol) by treatment with lithium tert-butyl acetate according to general procedure K (method b). Obtained as a yellow oil (8.306 g, 81%).

Workup

  1. customprepared by the following procedure
  2. customwas degassed
  3. temperatureThe reaction mixture was refluxed for 15 h
  4. customevaporated to dryness [Synlett 2000 (6), 829-831]
  5. temperatureat reflux for 16 h
  6. concentrationConcentrated in vacuum to about 100 mL
  7. additiondiluted with EtOAc
  8. washwashed with sat. NaHCO3-solution and brine
  9. dry with materialdried over Na2SO4
  10. customRemoval of the solvent in vacuum
  11. waitleft a brown residue, which
  12. customwas purified by silica gel column chromatography with cyclohexane/EtOAc

Sources & evidence

ORD record
ord-bd369046b6ac47c498f5c8d2b755e567
Source dataset
uspto-grants-2005_09
Patent number
US06949542B2

Linked notes

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