Ammonia methanol → 2-(5-fluoro-2-methyl-6,7-dihydrocyclopenta[e]indazol-8(2H)-ylidene)ethanamine

HRID 887787Notes

Reaction equation

HRID 887787 reaction equation
[F:1][C:2]1[C:3]2[CH2:14][CH2:13][C:12](=[CH:15][C:16]#[N:17])[C:4]=2[C:5]2[C:9]([CH:10]=1)=[N:8][N:7]([CH3:11])[CH:6]=2.N.CO>O1CCCC1.CO.[Co]>[F:1][C:2]1[C:3]2[CH2:14][CH2:13][C:12](=[CH:15][CH2:16][NH2:17])[C:4]=2[C:5]2[C:9]([CH:10]=1)=[N:8][N:7]([CH3:11])[CH:6]=2

Participants

5

Reactant 2

HCID 21705897Ammonia methanolHCID 68699726(5-fluoro-2-methyl-6,7-dihydrocyclopenta[e]indazol-8(2H)-ylidene)acetonitrile

Product 1

HCID 686997512-(5-fluoro-2-methyl-6,7-dihydrocyclopenta[e]indazol-8(2H)-ylidene)ethanamineYield 99%

Reagents, catalysts & solvents 2

HCID 104730CobaltCatalystHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of (5-fluoro-2-methyl-6,7-dihydrocyclopenta[e]indazol-8(2H)-ylidene)acetonitrile (156 mg, 0.686 mmol) in tetrahydrofuran/methanol (5 mL/5 mL) were added Raney cobalt (1.5 g) and 2M ammonia/methanol solution (2 mL), and the mixture was stirred under a hydrogen atmosphere at room temperature for 4 hr. The catalyst was filtered off through celite, and the filtrate was concentrated under reduced pressure to give the title compound (157 mg, yield 99%).

Workup

  1. filtrationThe catalyst was filtered off through celite
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-466a0fb0e9ce4f74b7864cbc1c30a81b
Source dataset
uspto-grants-2012_08
Patent number
US08247429B2

Reaction notes

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