Tetrahydrofuran → HCID 86627055, compound

HRID 2097539Notes

Reaction equation

HRID 2097539 reaction equation
O1CCCC1.[F:6][CH2:7][CH2:8][OH:9].[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][CH2:8][CH2:7][F:6]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 97372-FluoroethanolHCID 24758Sodium hydrideHCID 66602679HCID 66602679, compound

Product 1

HCID 86627055HCID 86627055, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 15 ml of dehydrated tetrahydrofuran solution containing 1.02 g (16 mmol) of 2-fluoroethanol was added 0.32 g (8.0 mmol) of sodium hydride (60% dispersed material in mineral oil) under ice-cooling, and the mixture was stirred at room temperature for 30 minutes. Then, 0.90 g (1.6 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 3 hours. 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 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=7:3 (V/V)), and the fractions containing the desired compound were concentrated under reduced pressure to obtain 802 mg of the title compound as a white solid. (Yield: 91%)

Workup

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

Sources & evidence

ORD record
ord-cd4e23cd43ba409393e03d2f3c9dcde9
Source dataset
uspto-grants-2013_05
Patent number
US08450319B2

Reaction notes

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