Hydrogen Bromide → HCID 24738994, compound

HRID 731649Notes

Reaction equation

HRID 731649 reaction equation
Br[CH2:2][C:3]([C:5]1[C:6]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[N:7][O:8][C:9]=1[CH3:10])=O.[NH2:17][C:18]1[CH:23]=[CH:22][C:21]([I:24])=[CH:20][N:19]=1.Br.C(N(CC)CC)C>C(O)C>[I:24][C:21]1[CH:22]=[CH:23][C:18]2[N:19]([CH:2]=[C:3]([C:5]3[C:6]([C:11]4[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=4)=[N:7][O:8][C:9]=3[CH3:10])[N:17]=2)[CH:20]=1

Participants

6

Reactant 4

HCID 260Hydrogen BromideHCID 8471TriethylamineHCID 885792-Pyridinamine, 5-iodo-HCID 27355314-(Bromoacetyl)-5-methyl-3-phenylisoxazole

Product 1

HCID 24738994HCID 24738994, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4-(bromoacetyl)-5-methyl-3-phenylisoxazole (commercially available) (420 mg, 1.5 mmol) and 2-amino-5-iodopyridine (330 mg, 1.5 mmol) in ethanol (6.7 mL) containing hydrobromic acid (48%, 84 μL, 0.75 mmol) and triethylamine (105 μL, 0.75 mmol) was heated under reflux under argon overnight. After cooling to room temperature, the mixture was evaporated and poured onto hydrochloric acid (0.5 N) and extracted with ethyl acetate. The combined organic layers were then washed with water and brine, dried over sodium sulphate and evaporated to leave a yellow oil. Purification by chromatography (SiO2, dichloromethane:methanol=100:0 to 95:5) afforded the title compound (170 mg, 28%) which was obtained as a light yellow solid. MS: m/e=402.1 [M+H]+.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux under argon overnight
  3. customthe mixture was evaporated
  4. additionpoured onto hydrochloric acid (0.5 N)
  5. extractionextracted with ethyl acetate
  6. washThe combined organic layers were then washed with water and brine
  7. dry with materialdried over sodium sulphate
  8. customevaporated
  9. customto leave a yellow oil
  10. customPurification by chromatography (SiO2, dichloromethane:methanol=100:0 to 95:5)

Sources & evidence

ORD record
ord-d970121bfba24599ac3dacd859df773b
Source dataset
uspto-grants-2009_09
Patent number
US07585874B2

Reaction notes

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