Isopropanol → HCID 66602443, compound

HRID 2097538Notes

Reaction equation

HRID 2097538 reaction equation
O1CCCC1.[CH:6]([OH:9])([CH3:8])[CH3:7].[H-].[Na+].[Br:12][C:13]1[N:30]([CH2:31][O:32][CH2:33][CH2:34][Si:35]([CH3:38])([CH3:37])[CH3:36])[C:16]2[CH:17]=[N:18][N:19]([CH2:22][O:23][CH2:24][CH2:25][Si:26]([CH3:29])([CH3:28])[CH3:27])[C:20](=[O:21])[C:15]=2[C:14]=1[CH2:39]Br>O>[Br:12][C:13]1[N:30]([CH2:31][O:32][CH2:33][CH2:34][Si:35]([CH3:38])([CH3:37])[CH3:36])[C:16]2[CH:17]=[N:18][N:19]([CH2:22][O:23][CH2:24][CH2:25][Si:26]([CH3:29])([CH3:28])[CH3:27])[C:20](=[O:21])[C:15]=2[C:14]=1[CH2:39][O:9][CH:6]([CH3:8])[CH3:7]

Participants

6

Reactant 4

HCID 3776IsopropanolHCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 66602679HCID 66602679, compound

Product 1

HCID 66602443HCID 66602443, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 2 ml of dehydrated tetrahydrofuran solution containing 1 ml of isopropanol was added 155 mg of sodium hydride (55% dispersed material in mineral oil), the mixture was stirred at room temperature for 20 minutes, then, 272 mg (0.48 mmol) of 2-bromo-3-bromomethyl-1,5-bis(2-trimethylsilylethoxymethyl)-1,5-dihydropyrrolo[2,3-d]pyridazin-4-one obtained in Reference example 25-(a) was further added to the mixture, and the mixture was stirred at room temperature for 1 hour. After completion of the reaction, water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer after separation was washed successively with water and then with a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate, and then, concentrated under reduced pressure. The obtained residue was applied to silica gel column chromatography (Eluent; hexane:ethyl acetate=9:1 (V/V)), and the fractions containing the desired compound were concentrated under reduced pressure to obtain 176 mg of the title compound as a colorless oil. (Yield: 67%)

Workup

  1. additionwas further added to the mixture
  2. stirringthe mixture was stirred at room temperature for 1 hour
  3. additionwas added to the reaction mixture
  4. extractionthe mixture was extracted with ethyl acetate
  5. customThe organic layer after separation
  6. washwas washed successively with water
  7. dry with materialwith a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. additionthe fractions containing the desired compound
  10. concentrationwere concentrated under reduced pressure

Sources & evidence

ORD record
ord-de8c69b722fc42e395ff9963ab6e2f66
Source dataset
uspto-grants-2013_05
Patent number
US08450319B2

Reaction notes

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