1-(1,3-Dioxaindan-5-yl)-2-bromoethan-1-one → HCID 11335851, compound

HRID 2356243Notes

Reaction equation

HRID 2356243 reaction equation
[CH:1]1([CH2:4][O:5][C:6]2[N:11]=[N:10][C:9]([NH2:12])=[CH:8][CH:7]=2)[CH2:3][CH2:2]1.Br[CH2:14][C:15]([C:17]1[CH:22]=[CH:21][C:20]2[O:23][CH2:24][O:25][C:19]=2[CH:18]=1)=O.C(=O)([O-])O.[Na+]>C(O)C>[CH2:24]1[O:23][C:20]2[CH:21]=[CH:22][C:17]([C:15]3[N:12]=[C:9]4[CH:8]=[CH:7][C:6]([O:5][CH2:4][CH:1]5[CH2:2][CH2:3]5)=[N:11][N:10]4[CH:14]=3)=[CH:18][C:19]=2[O:25]1

Participants

5

Reactant 3

HCID 2437771-(1,3-Dioxaindan-5-yl)-2-bromoethan-1-oneHCID 516892Sodium Bicarbonate2×HCID 68456032HCID 68456032, compound

Product 1

HCID 11335851HCID 11335851, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A stirred mixture of 6-cyclopropylmethoxypyridazin-3-amine (110 mg), 2-bromo-1-(3,4-methylenedioxyphenyl]ethanone (162 mg), sodium hydrogen carbonate (84 mg, 1 mmol) and ethanol (5 mL) was heated under reflux for 3 hours. Sodium hydrogen carbonate (56 mg) was added and the mixture was refluxed for a further 0.5 hour. The mixture was evaporated. The residue was extracted with chloroform (50 mL) and the extract washed with saturated, aqueous, sodium chloride solution (50 mL), dried (MgSO4) and evaporated. The residue was purified by flash chromatography on silica gel. Elution with 1-3% methanol in dichloromethane afforded Compound 43 (162 mg). 1H n.m.r. (CDCl3) δ 0.33-0.43, m, 2H; 0.62-0.72, m, 2H; 1.22-1.44, m, 1H; 4.13, d, 2H; 6.0, s, 2H; 6.72, d, 1H; 6.86, d, 1H; 7.38, s, 1H; 7.40, d, 1H; 7.78, d, 1H; 7.90, s, 1H.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 3 hours
  3. temperaturethe mixture was refluxed for a further 0.5 hour
  4. customThe mixture was evaporated
  5. extractionThe residue was extracted with chloroform (50 mL)
  6. washthe extract washed with saturated, aqueous, sodium chloride solution (50 mL)
  7. dry with materialdried (MgSO4)
  8. customevaporated
  9. customThe residue was purified by flash chromatography on silica gel
  10. washElution with 1-3% methanol in dichloromethane afforded Compound 43 (162 mg)

Sources & evidence

ORD record
ord-1f62006508324715977d05f8678ab504
Source dataset
uspto-grants-2010_07
Patent number
US07759349B2

Reaction notes

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