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

HRID 530816Notes

Reaction equation

HRID 530816 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][N:31]1[C:39]2[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=2)[C:33]([C@H:40]2[CH2:42][C@@H:41]2[CH2:43]O)=[N:32]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][CH2:43][C@H:41]2[CH2:42][C@@H:40]2[C:33]2[C:34]3[C:39](=[CH:38][CH:37]=[CH:36][CH:35]=3)[N:31]([CH3:30])[N:32]=2)[CH:3]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 904191185-Bromo-1-methyl-1,2-dihydropyridazine-3,6-dioneHCID 90419223((1S,2S)-2-(1-methyl-1H-indazol-3-yl)cyclopropyl)methanol

Product 1

HCID 904193174-bromo-2-methyl-6-(((1S,2S)-2-(1-methyl-1H-indazol-3-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 (300 mg, 1.485 mmol) in THF (20 mL) at 0° C. was added PPh3 (781 mg, 2.97 mmol) and ((1S,2S)-2-(1-methyl-1H-indazol-3-yl)cyclopropyl)methanol (300 mg, 1.485 mmol) followed by dropwise addition of DIAD (0.6 mL, 2.97 mmol). The reaction mixture was warmed to ambient temperature. After stirred for 2 h, the mixture was concentrated. The residue was purified by column chromatography on silica gel, eluting with PE/EA (2/1) 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 (2/1)

Sources & evidence

ORD record
ord-9f9223e7cd0e4d898ab21e8717e44724
Source dataset
uspto-grants-2016_05
Patent number
US09353104B2

Reaction notes

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