Triphenylphosphine → 4-bromo-2-methyl-6-(((1S,2S)-2-(5-methylpyridin-2-yl)cyclopropyl)methoxy)pyridazin-3(2H)-one

HRID 530788Notes

Reaction equation

HRID 530788 reaction equation
[Br:1][C:2]1[C:7](=[O:8])[N:6]([CH3:9])[NH:5][C:4](=[O:10])[CH:3]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[CH3:30][C:31]1[CH:32]=[CH:33][C:34]([C@H:37]2[CH2:39][C@@H:38]2[CH2:40]O)=[N:35][CH:36]=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[Br:1][C:2]1[C:7](=[O:8])[N:6]([CH3:9])[N:5]=[C:4]([O:10][CH2:40][C@H:38]2[CH2:39][C@@H:37]2[C:34]2[CH:33]=[CH:32][C:31]([CH3:30])=[CH:36][N:35]=2)[CH:3]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 89417287((1S,2S)-2-(5-methylpyridin-2-yl)cyclopropyl)methanolHCID 904191185-Bromo-1-methyl-1,2-dihydropyridazine-3,6-dione

Product 1

HCID 904543854-bromo-2-methyl-6-(((1S,2S)-2-(5-methylpyridin-2-yl)cyclopropyl)methoxy)pyridazin-3(2H)-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-bromo-1-methyl-1,2-dihydropyridazine-3,6-dione (100 mg, 0.49 mmol) in THF (3 mL) at 0° C. was added triphenyl phosphorous (257 mg, 0.98 mmol) and ((1S,2S)-2-(5-methylpyridin-2-yl)cyclopropyl)methanol (4) (80 mg, 0.49 mmol) followed by dropwise addition of DIAD (198 mg, 0.98 mmol). The reaction mixture was warmed to ambient temperature. After stirred for 1 h, the mixture was concentrated. The residue was purified by column chromatography on silica gel, eluting with PE/EA (1/2) to give the title compound as oil.

Workup

  1. concentrationthe mixture was concentrated
  2. customThe residue was purified by column chromatography on silica gel
  3. washeluting with PE/EA (1/2)

Sources & evidence

ORD record
ord-069a268b7a47446094a5686f1226525b
Source dataset
uspto-grants-2016_05
Patent number
US09353104B2

Reaction notes

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