Tri-o-tolylphosphine → HCID 21830726, compound

HRID 1600947Notes

Reaction equation

HRID 1600947 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][CH2:8][CH:9]([OH:12])[CH:10]=[CH2:11])[CH:2]=1.[Cl:13][C:14]1[CH:15]=[C:16]([C:20]2[CH:25]=[CH:24][C:23](OS(C(F)(F)F)(=O)=O)=[CH:22][CH:21]=2)[CH:17]=[CH:18][CH:19]=1.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(N(CC)CC)C>[Cl:13][C:14]1[CH:15]=[C:16]([C:20]2[CH:21]=[CH:22][C:23]([CH2:11][CH2:10][C:9](=[O:12])[CH2:8][CH2:7][C:3]3[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=3)=[CH:24][CH:25]=2)[CH:17]=[CH:18][CH:19]=1

Participants

6

Reactant 3

HCID 80271Tri-o-tolylphosphineHCID 17866850HCID 17866850, compoundHCID 218306693′-Chloro[1,1′-biphenyl]-4-yl 1,1,1-trifluoromethanesulfonate

Product 1

HCID 21830726HCID 21830726, compoundYield 28.7%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 8471TriethylamineSolvent

Procedure

Prepared according to the method described in Example 7b) from (±)-5-(3-pyridyl)-1-penten-3-ol (Example 7a, 0.66 g), 3'-chloro-4-trifluoromethanesulfonyloxybiphenyl (1.34 g), palladium(II) acetate (0.09 g), tri-o-tolylphosphine (5 ml) and triethylamine (1 ml) at 80° C. for 5 hours. Work up and purification by column chromatography over silica eluting with dichloromethane:methanol (19:1) gave (±)-1-(3'-chlorobiphenyl-4-yl)-5-(3-pyridyl)-3-pentanone (0.4 g). The latter was immediately dissolved in methanol (10 ml), cooled to 0° C. and sodium borohydride (0.043 g) added. The reaction mixture was stirred at 25° C. for 2 hours and was then concentrated under reduced pressure. Water was added to the residue and the mixture extracted with ethyl acetate. The combined extracts were dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography over silica eluting with ethyl acetate. Conversion to the oxalate salt upon treatment with excess saturated ethereal oxalic acid gave the title compound as a solid (0.094 g).

Workup

  1. customPrepared
  2. customat 80° C.
  3. customfor 5 hours
  4. customWork up and purification by column chromatography over silica eluting with dichloromethane:methanol (19:1)

Sources & evidence

ORD record
ord-b97096d5b6124a3d969e8eb2be589e0f
Source dataset
uspto-grants-1999_11
Patent number
US05977105

Reaction notes

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