Sodium hydride → (5-fluoro-2-methyl-6,7-dihydrocyclopenta[e]indazol-8(2H)-ylidene)acetonitrile

HRID 887786Notes

Reaction equation

HRID 887786 reaction equation
[H-].[Na+].[C:3]([CH2:5]P(=O)(OCC)OCC)#[N:4].[F:14][C:15]1[C:16]2[CH2:27][CH2:26][C:25](=O)[C:17]=2[C:18]2[C:22]([CH:23]=1)=[N:21][N:20]([CH3:24])[CH:19]=2.[Cl-].[NH4+]>O1CCCC1.C(OCC)(=O)C>[F:14][C:15]1[C:16]2[CH2:27][CH2:26][C:25](=[CH:5][C:3]#[N:4])[C:17]=2[C:18]2[C:22]([CH:23]=1)=[N:21][N:20]([CH3:24])[CH:19]=2

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 75676Diethyl (cyanomethyl)phosphonateHCID 59145895HCID 59145895, compound

Product 1

HCID 68699726(5-fluoro-2-methyl-6,7-dihydrocyclopenta[e]indazol-8(2H)-ylidene)acetonitrileYield 64%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of 60% sodium hydride (59.0 mg, 1.48 mmol) in tetrahydrofuran (8 mL) was added diethyl cyanomethylphosphonate (260 μL, 1.60 mmol) at room temperature, and the mixture was stirred for 15 min. A suspension of 5-fluoro-2-methyl-6,7-dihydrocyclopenta [e] indazol-8(2H)-one (252 mg, 1.23 mmol) in tetrahydrofuran (4 mL) was added thereto, and the mixture was stirred at room temperature for 4 hr. Saturated aqueous ammonium chloride solution was added to the reaction solution, and the mixture was diluted with ethyl acetate, washed with water and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The obtained crystals were washed with diisopropyl ether to give the title compound (178 mg, yield 64%).

Workup

  1. additionwas added
  2. stirringthe mixture was stirred at room temperature for 4 hr
  3. washwashed with water and saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. washThe obtained crystals were washed with diisopropyl ether

Sources & evidence

ORD record
ord-a91566cbf58344d7a403ec8f02c29d42
Source dataset
uspto-grants-2012_08
Patent number
US08247429B2

Reaction notes

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