HCID 86677031, compound → HCID 71270347, compound

HRID 927114Notes

Reaction equation

HRID 927114 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:23]=[O:24])[N:12]=[N:13][C:14]=1[O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:25]1([Mg]Br)[CH2:27][CH2:26]1>C1COCC1>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:23]([CH:25]2[CH2:27][CH2:26]2)[OH:24])[N:12]=[N:13][C:14]=1[O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 86677031HCID 86677031, compound2×HCID 178418630HCID 178418630, compound

Product 1

HCID 71270347HCID 71270347, compoundYield 61.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
2.5 °C

Procedure

5,6-bis(Benzyloxy)pyridazine-3-carbaldehyde (Intermediate 63; 0.5 g, 1.562 mmol) was dissolved into THF (10 ml) and cooled to 0-5° C. under a nitrogen atmosphere. A solution of cyclopropyl magnesium bromide in THF (0.5 M, 4.7 ml, 2.34 mmol) was added at 0-5° C., and reaction mixture was stirred at room temperature for 4 hours. Upon completion, the reaction was quenched by addition of ethyl acetate and saturated aqueous ammonium chloride solution and extracted into ethyl acetate (2×50 ml). The combined organics were separated and washed with brine, dried (Na2SO4) and concentrated in vacuo. The crude compound was purified by column chromatography (silica, 0-2% methanol in dichloromethane) to afford (5,6-bis(benzyloxy)pyridazin-3-yl)(cyclopropyl)methanol (0.35 g, 61.9% yield).

Workup

  1. customreaction mixture
  2. customUpon completion, the reaction was quenched by addition of ethyl acetate and saturated aqueous ammonium chloride solution
  3. extractionextracted into ethyl acetate (2×50 ml)
  4. customThe combined organics were separated
  5. washwashed with brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated in vacuo
  8. customThe crude compound was purified by column chromatography (silica, 0-2% methanol in dichloromethane)

Sources & evidence

ORD record
ord-c064a7338cba472e872197334cc02c5d
Source dataset
uspto-grants-2016_03
Patent number
US09290456B2

Reaction notes

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