Thionyl Chloride → HCID 69486831, compound

HRID 498235Notes

Reaction equation

HRID 498235 reaction equation
CO[C:3](=[O:18])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]2[N:11]=[N:12][C:13]([O:16][CH3:17])=[CH:14][CH:15]=2)[CH:5]=1.[C:19]([C:22]1[CH:23]=C(B(O)O)C=C[CH:27]=1)(O)=O.ClC1N=N[C:35]([O:38]C)=[CH:36]C=1.[O:40]=S(Cl)Cl>C(#N)C.C([O-])([O-])=O.[Na+].[Na+]>[C:22]([O:40][C:35](=[O:38])[CH2:36][C:3]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]2[N:11]=[N:12][C:13]([O:16][CH3:17])=[CH:14][CH:15]=2)[CH:5]=1)=[O:18])([CH3:19])([CH3:27])[CH3:23]

Participants

7

Reactant 4

HCID 24386Thionyl ChlorideHCID 744033-Chloro-6-methoxypyridazineHCID 27339573-Carboxyphenylboronic acidHCID 69489774HCID 69489774, compound

Product 1

HCID 69486831HCID 69486831, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 10340Sodium CarbonateSolvent

Procedure

The title compound was prepared from 3-(6-methoxy-pyridazin-3-yl)-benzoic acid methyl ester [prepared by the following procedure: A mixture of 3-carboxyphenyl-boronic acid (7.11 g, 42.8 mmol) and 3-chloro-6-methoxy-pyridazine [CAS-No. 1722-10-7] (6.19 g, 42.8 mmol) in acetonitrile (212 mL) and 0.4M Na2CO3-solution (212 mL) was degassed and Pd(Ph3P)4 (2.47 g, 5 mol %) was added. The reaction mixture was refluxed for 16 h, evaporated to dryness (cf. Synlett 2000, 829). The residue was suspended in MeOH (630 mL) and SOCl2 (15.5 mL, 214.1 mmol) was added dropwise at 23° C. and the reaction mixture was refluxed for 4 h. Evaporated to dryness, taken up in EtOAc, washed with sat. NaHCO3-solution and brine, dried over Na2SO4. Removal of the solvent in vacuum left a brown oil, which was purified by silica gel column chromatography with cyclohexane/EtOAc.] (5.41 g, 22.15 mmol) by treatment with lithium tert-butyl acetate according to general procedure K (method b). Obtained as a yellow oil (6.39 g).

Workup

  1. customprepared by the following procedure
  2. customwas degassed
  3. additionPd(Ph3P)4 (2.47 g, 5 mol %) was added
  4. temperatureThe reaction mixture was refluxed for 16 h
  5. customevaporated to dryness (cf. Synlett 2000, 829)
  6. temperaturethe reaction mixture was refluxed for 4 h
  7. customEvaporated to dryness
  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 oil, which
  12. customwas purified by silica gel column chromatography with cyclohexane/EtOAc

Sources & evidence

ORD record
ord-518389f48b674ecc9060e13c3755c285
Source dataset
uspto-grants-2005_09
Patent number
US06949542B2

Reaction notes

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