Sodium hydride → HCID 86647344, compound

HRID 1958074Notes

Reaction equation

HRID 1958074 reaction equation
[H-].[Na+].[CH2:3]([C:7]1[C:11]([CH2:12][OH:13])=[C:10]([CH3:14])[O:9][N:8]=1)[CH2:4][CH2:5][CH3:6].[Cl:15][C:16]1[N:17]=[N:18][C:19](Cl)=[CH:20][CH:21]=1>C1COCC1>[CH2:3]([C:7]1[C:11]([CH2:12][O:13][C:19]2[N:18]=[N:17][C:16]([Cl:15])=[CH:21][CH:20]=2)=[C:10]([CH3:14])[O:9][N:8]=1)[CH2:4][CH2:5][CH3:6]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 673313,6-DichloropyridazineHCID 66599297(3-Butyl-5-methyl-isoxazol-4-yl)-methanol

Product 1

HCID 86647344HCID 86647344, compoundYield 78.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To a stirred suspension of NaH (258 mg of a 55% dispersion in mineral oil) in THF (9 mL) at 0° C. under argon, was added a solution of (3-butyl-5-methyl-isoxazol-4-yl)-methanol (1.0 g, 5.9 mmol) in THF (18 mL) dropwise. The reaction mixture was warmed to room temperature. After 30 min the reaction mixture was cooled to 0° C. and a solution of 3,6-dichloropyridazine (908 mg, 6.1 mmol) in THF (18 mL) was added dropwise. After 16 h the reaction mixture was warmed to room temperature then quenched with water and extracted with ethyl acetate. The combined organic phases were dried, filtered and concentrated then purified by chromatography (silica, 10 to 60% ethyl acetate in heptane) to give the title compounds (1.31 g, 66%) as a light yellow liquid.

Workup

  1. temperatureAfter 30 min the reaction mixture was cooled to 0° C.
  2. temperatureAfter 16 h the reaction mixture was warmed to room temperature
  3. customthen quenched with water
  4. extractionextracted with ethyl acetate
  5. customThe combined organic phases were dried
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customthen purified by chromatography (silica, 10 to 60% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-9266ef84fe6a4887bf3f08f401f8911a
Source dataset
uspto-grants-2013_04
Patent number
US08410104B2

Reaction notes

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