Bromotrichloromethane → HCID 69673559, compound

HRID 2283246Notes

Reaction equation

HRID 2283246 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]2[N:10]=[N:11][CH:12]=[C:13]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:14]=2[C:15]2[O:16][CH2:17][CH:18]([C:20]([O:22][CH3:23])=[O:21])[N:19]=2)[CH:6]=[CH:7][CH:8]=1.C1CCN2C(=NCCC2)CC1.BrC(Cl)(Cl)Cl>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]2[N:10]=[N:11][CH:12]=[C:13]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:14]=2[C:15]2[O:16][CH:17]=[C:18]([C:20]([O:22][CH3:23])=[O:21])[N:19]=2)[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 6383BromotrichloromethaneHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 69673552HCID 69673552, compound2×

Product 1

HCID 69673559HCID 69673559, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl 2-(3-(3-methoxyphenyl)-5-phenylpyridazin-4-yl)-4,5-dihydrooxazole-4-carboxylate (compound 25) (60 mg, 0.16 mmol) in DCM (3 mL), DBU (76 mg, 0.5 mmol), bromotrichloromethane (83 mg, 0.41 mmol) was added at 0° C., stirred for 3 h and then warmed to rt. Reaction was quenched by addition of sat. sodium bicarbonate solution, extracted with DCM (2×25 mL), washed with brine (1×5 mL) and dried over anhydrous Na2SO4. Evaporation of solvent under reduced pressure gave the crude product that was purified by column chromatography (100-200 mesh silica gel, 35% EtOAc-Hexane) to furnish methyl 2-(3-(3-methoxyphenyl)-5-phenylpyridazin-4-yl)oxazole-4-carboxylate (compound 26) (35 mg, 59%) as an off white solid.

Workup

  1. customReaction
  2. customwas quenched by addition of sat. sodium bicarbonate solution
  3. extractionextracted with DCM (2×25 mL)
  4. washwashed with brine (1×5 mL)
  5. dry with materialdried over anhydrous Na2SO4
  6. customEvaporation of solvent under reduced pressure
  7. customgave the crude product that
  8. customwas purified by column chromatography (100-200 mesh silica gel, 35% EtOAc-Hexane)

Sources & evidence

ORD record
ord-4ff20d68b1994e2eb81bfc849954d0ae
Source dataset
uspto-grants-2015_09
Patent number
US09145372B2

Reaction notes

Loading…