Boron trifluoride etherate → HCID 59191656, compound

HRID 447094Notes

Reaction equation

HRID 447094 reaction equation
[Cl:1][C:2]1[N:7]=[N:6][C:5]([C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=O)=[C:4]([CH3:16])[C:3]=1[CH3:17].[CH2:18]([SH:21])[CH2:19][SH:20].B(F)(F)F.CCOCC>C(Cl)Cl>[Cl:1][C:2]1[N:7]=[N:6][C:5]([C:8]2([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)[S:21][CH2:18][CH2:19][S:20]2)=[C:4]([CH3:16])[C:3]=1[CH3:17]

Participants

5

Reactant 3

HCID 8000Boron trifluoride etherate2×HCID 109021,2-Ethanedithiol2×HCID 59191581HCID 59191581, compound

Product 1

HCID 59191656HCID 59191656, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a DCM solution of (6-chloro-4,5-dimethyl-pyridazin-3-yl)-phenyl-methanone (300 mg, 1.22 mmol) is added 1,2-ethandithiol (0.408 ml, 4.86 mmol) and BF3.OEt2 (0.154 ml, 1.216 mmol) at 0° C. under nitrogen atmosphere. The reaction mixture is stirred at room temperature for 16 h. The reaction was charged with BF3.OEt2 (0.154 ml, 1.216 mmol) and 1,2-ethandithiol (0.408 ml, 4.86 mmol), and heated at 40° C. for 6 h. The reaction is quenched with sat. NaHCO3 at 0° C. and organic phase is washed with brine. The organic layer is dried over Na2SO4, filtered and concentrated to afford a yellow solid. The residue is loaded on silica gel and purified by flash chromatography, eluting with 20-80% EtOAc: heptane. Fractions containing the desired product are combined and concentrated to afford a white solid (280 mg, 73%).

Workup

  1. temperatureheated at 40° C. for 6 h
  2. customThe reaction is quenched with sat. NaHCO3 at 0° C.
  3. washorganic phase is washed with brine
  4. dry with materialThe organic layer is dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto afford a yellow solid
  8. custompurified by flash chromatography
  9. washeluting with 20-80% EtOAc
  10. additionFractions containing the desired product
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-a5cde54f70164dea9ee45b4eeadd1994
Source dataset
uspto-grants-2013_07
Patent number
US08481542B2

Reaction notes

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