Azobisisobutyronitrile → 3-bromomethyl-2-oxazol-2-yl-1-phenyl-1H-[1,8]naphthyridin-4-one

HRID 1887786Notes

Reaction equation

HRID 1887786 reaction equation
N(C(C)(C)C#N)=NC(C)(C)C#N.[Br:13]N1C(=O)CCC1=O.[CH3:21][C:22]1[C:31](=[O:32])[C:30]2[C:25](=[N:26][CH:27]=[CH:28][CH:29]=2)[N:24]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[C:23]=1[C:39]1[O:40][CH:41]=[CH:42][N:43]=1>C(Cl)(Cl)(Cl)Cl.O>[Br:13][CH2:21][C:22]1[C:31](=[O:32])[C:30]2[C:25](=[N:26][CH:27]=[CH:28][CH:29]=2)[N:24]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[C:23]=1[C:39]1[O:40][CH:41]=[CH:42][N:43]=1

Participants

6

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 712082443-methyl-2-oxazol-2-yl-1-phenyl-1H-[1,8]naphthyridin-4-one

Product 1

HCID 866757623-bromomethyl-2-oxazol-2-yl-1-phenyl-1H-[1,8]naphthyridin-4-oneYield 47.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 2,2′-azobis(2-methylpropionitrile) (AIBN, 43.4 mg, 0.265 mmol), N-bromosuccinimide (345 mg, 1.94 mmol) and 3-methyl-2-oxazol-2-yl-1-phenyl-1H-[1,8]naphthyridin-4-one (535 mg, 1.76 mmol) in carbon tetrachloride (22.0 mL) was heated at 90° C. for 2 hr. The reaction was cooled to 25° C. and sat overnight. The reaction was diluted with water (30 mL) and extracted into methylene chloride (2×50 mL). The combined organics were then washed with a saturated aqueous solution of sodium bicarbonate (2×50 mL), dried over sodium sulfate, filtered and concentrated in vacuo. The residue was dissolved in methylene chloride and methanol, treated with silica gel, re-concentrated and dried in vacuo. Flash chromatography (40 g, 15%-40% ethyl acetate-hexanes) gave 3-bromomethyl-2-oxazol-2-yl-1-phenyl-1H-[1,8]naphthyridin-4-one (321.7 mg, 47.7%).

Workup

  1. temperatureThe reaction was cooled to 25° C.
  2. extractionextracted into methylene chloride (2×50 mL)
  3. washThe combined organics were then washed with a saturated aqueous solution of sodium bicarbonate (2×50 mL)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. dissolutionThe residue was dissolved in methylene chloride
  8. additionmethanol, treated with silica gel
  9. concentrationre-concentrated
  10. customdried in vacuo

Sources & evidence

ORD record
ord-a678f171a3174131a0457fd1a5d463b6
Source dataset
uspto-grants-2013_08
Patent number
US08501732B2

Reaction notes

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