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4-Fluorobenzylic alcohol → 1-Benzyl-7-(4-fluorobenzyloxy)-2-methylpyrrolo[2,3-d]pyridazine

HRID 1734527
Notes
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Reaction equation

HRID 1734527 reaction equation
CC(C)([O-])C.[K+].[F:7][C:8]1[CH:15]=[CH:14][C:11]([CH2:12][OH:13])=[CH:10][CH:9]=1.[CH2:16]([N:23]1[C:27]2=[C:28](Cl)[N:29]=[N:30][CH:31]=[C:26]2[CH:25]=[C:24]1[CH3:33])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CN1CCCC1=O>[CH2:16]([N:23]1[C:27]2=[C:28]([O:13][CH2:12][C:11]3[CH:14]=[CH:15][C:8]([F:7])=[CH:9][CH:10]=3)[N:29]=[N:30][CH:31]=[C:26]2[CH:25]=[C:24]1[CH3:33])[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 680224-Fluorobenzylic alcoholHCID 194377481-Benzyl-7-chloro-2-methylpyrrolo[2,3-d]pyridazineHCID 23665647Potassium tert-butoxide

Product 1

HCID 194377621-Benzyl-7-(4-fluorobenzyloxy)-2-methylpyrrolo[2,3-d]pyridazine

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent2×

Procedure

32.65 g (291 mmol) of potassium tert-butoxide and 1.54 g (5.82 mmol) of [18]crown-6 (98% strength) are added successively to a solution of 21.8 g (173 mmol) of 4-fluorobenzyl alcohol in 150 ml of anhydrous N-methylpyrrolidone. This mixture is stirred at room temperature for 1 h. A solution of 15.0 g (58.2 mmol) of 1-benzyl-7-chloro-2-methylpyrrolo[2,3-d]pyridazine in 100 ml of anhydrous N-methylpyrrolidone is subsequently added dropwise in the course of 30 min. The mixture is stirred at room temperature for a further 15 min, then treated with 500 ml of ice-water and extracted with 3×400 ml of ethyl acetate. The organic extracts are washed with 3×300 ml of water and subsequently dried over magnesium sulfate. After concentration and crystallization from diisopropyl ether, 12.95 g (64%) of the title compound are isolated. M.p.: 127°-132° C.

Workup

  1. stirringThe mixture is stirred at room temperature for a further 15 min
  2. extractionextracted with 3×400 ml of ethyl acetate
  3. washThe organic extracts are washed with 3×300 ml of water
  4. dry with materialsubsequently dried over magnesium sulfate
  5. concentrationAfter concentration and crystallization from diisopropyl ether, 12.95 g (64%) of the title compound
  6. customare isolated

Sources & evidence

ORD record
ord-a35c6760b2df472c893b8d9bcbe7e10e
Source dataset
uspto-grants-1996_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05534515

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes