HCID 69673085, compound → HCID 69673945, compound

HRID 2283251Notes

Reaction equation

HRID 2283251 reaction equation
Br[CH2:2][C:3]1[N:4]=[C:5]([C:8]2[C:13]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[CH:12][N:11]=[N:10][C:9]=2[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[O:6][CH:7]=1>CO.[Pd]>[C:20]1([C:9]2[N:10]=[N:11][CH:12]=[C:13]([C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:8]=2[C:5]2[O:6][CH:7]=[C:3]([CH3:2])[N:4]=2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

4

Reactant 1

HCID 69673085HCID 69673085, compound

Product 1

HCID 69673945HCID 69673945, compoundYield 6.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 4-(bromomethyl)-2-(3,5-diphenylpyridazin-4-yl)oxazole (250 mg, 0.64 mmol) in methanol (8 mL), Pd/C (80 mg, wt/wt) was added and the resulting reaction mixture was stirred under hydrogen atmosphere for 1.5 h. The reaction mixture was filtered through a celite bed, washed with methanol and concentrated under reduced pressure to obtain the crude product which was purified by preparative TLC to furnish 2-(3,5-diphenylpyridazin-4-yl)-4-methyloxazole (compound 20) (13.6 mg, 6.8%) as pale yellow gummy liquid.

Workup

  1. customthe resulting reaction mixture
  2. filtrationThe reaction mixture was filtered through a celite bed
  3. washwashed with methanol
  4. concentrationconcentrated under reduced pressure
  5. customto obtain the crude product which
  6. customwas purified by preparative TLC

Sources & evidence

ORD record
ord-284a1e70f5d84161a97f1d7e046b2b69
Source dataset
uspto-grants-2015_09
Patent number
US09145372B2

Reaction notes

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