2-Bromo-1-indanone → HCID 11219307, compound

HRID 2356253Notes

Reaction equation

HRID 2356253 reaction equation
[CH2:1]([O:4][C:5]1[N:10]=[N:9][C:8]([NH2:11])=[CH:7][CH:6]=1)[CH2:2][CH3:3].Br[CH:13]1[CH2:21][C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:14]1=O.C(=O)(O)[O-].[Na+]>C(O)C>[CH2:1]([O:4][C:5]1[CH:6]=[CH:7][C:8]2[N:9]([N:10]=1)[C:13]1[CH2:21][C:20]3[C:15]([C:14]=1[N:11]=2)=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH2:2][CH3:3]

Participants

5

Reactant 3

HCID 1372032-Bromo-1-indanoneHCID 516892Sodium BicarbonateHCID 105110476-Propoxypyridazin-3-amine

Product 1

HCID 11219307HCID 11219307, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A stirred mixture of 6-propoxypyridazin-3-amine (145 mg) and 2-bromo-1-indanone (200 mg) in ethanol (10 mL) was heated under reflux for 3 hours. The mixture was cooled and sodium bicarbonate (80 mg) was added. The mixture was stirred refluxed for 1 hour and then the ethanol was evaporated. The residue was extracted with chloroform and the extract washed with saturated, aqueous, sodium chloride solution, dried (MgSO4) and evaporated. The residue was purified by flash chromatography on silica gel. Elution with 1-2% methanol in dichloromethane afforded Compound 123 (30 mg) as a white solid. 1H n.m.r. (CDCl3) δ 1.12, t, 3H; 1.87, sextet, 2H; 3.85, s, 2H; 4.30, t, 2H; 6.64, d, 1H; 7.30, d, 1H; 7.40, t, 1H; 7.53, d, 1H; 7.80-7.88, m, 2H.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 3 hours
  3. temperatureThe mixture was cooled
  4. temperaturerefluxed for 1 hour
  5. customthe ethanol was evaporated
  6. extractionThe residue was extracted with chloroform
  7. washthe extract washed with saturated, aqueous, sodium chloride solution
  8. dry with materialdried (MgSO4)
  9. customevaporated
  10. customThe residue was purified by flash chromatography on silica gel
  11. washElution with 1-2% methanol in dichloromethane afforded Compound 123 (30 mg) as a white solid

Sources & evidence

ORD record
ord-0e1940dbace444868353fa66e6c6fc7a
Source dataset
uspto-grants-2010_07
Patent number
US07759349B2

Reaction notes

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