Triethylamine → HCID 86677039, compound

HRID 927126Notes

Reaction equation

HRID 927126 reaction equation
[CH2:1]([O:8][C:9]1[N:10]=[N:11][C:12]([CH:23]=[CH2:24])=[CH:13][C:14]=1[O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC1C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.[F:47][C:48]1[CH:53]=[C:52](I)[CH:51]=[CH:50][C:49]=1[C:55]([F:58])([F:57])[F:56].C(N(CC)CC)C>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(#N)C>[CH2:1]([O:8][C:9]1[N:10]=[N:11][C:12](/[CH:23]=[CH:24]/[C:52]2[CH:51]=[CH:50][C:49]([C:55]([F:57])([F:58])[F:56])=[C:48]([F:47])[CH:53]=2)=[CH:13][C:14]=1[O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 80271Tri-o-tolylphosphineHCID 27373432-fluoro-4-iodo-1-(trifluoromethyl)benzeneHCID 86677037HCID 86677037, compound2×

Product 1

HCID 86677039HCID 86677039, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

A vessel containing 3,4-bis(benzyloxy)-6-ethenylpyridazine (Intermediate 78, 1.09 g, 3.42 mmol), tris-(2-methylphenyl)phosphane (0.208 g, 0.685 mmol), 2-fluoro-4-iodo-1-(trifluoromethyl)benzene (1.191 g, 4.11 mmol) and palladium(II) acetate (0.038 g, 0.171 mmol) was evacuated and acetonitrile (10 ml) and triethylamine (9.07 ml, 65.1 mmol) were added in vacuo and then the mixture was flushed with nitrogen. The reaction was then heated in the microwave at 80° C. for 4 hours and, upon cooling, was diluted with dichloromethane and washed with saturated aqueous ammonium chloride solution. The organics were dried (MgSO4), filtered and solvent removed in vacuo to give a brown oil which was purified by column chromatography (silica, eluting with 30-100% dichloromethane in petrol) to yield 3,4-bis(benzyloxy)-6-[(E)-2-[3-fluoro-4-(trifluoromethyl)phenyl]ethenyl]pyridazine (1.1 g, 2.29 mmol, 67% yield).

Workup

  1. customwas evacuated
  2. customthe mixture was flushed with nitrogen
  3. temperatureupon cooling
  4. additionwas diluted with dichloromethane
  5. washwashed with saturated aqueous ammonium chloride solution
  6. dry with materialThe organics were dried (MgSO4)
  7. filtrationfiltered
  8. customsolvent removed in vacuo
  9. customto give a brown oil which
  10. customwas purified by column chromatography (silica, eluting with 30-100% dichloromethane in petrol)

Sources & evidence

ORD record
ord-1c5649e27ecb403a8866a17faeb629bb
Source dataset
uspto-grants-2016_03
Patent number
US09290456B2

Reaction notes

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