Water → 2-amino-5-(2-fluorophenyl)-4-methyl-1H-pyrrole-3-carbonitrile

HRID 565444Notes

Reaction equation

HRID 565444 reaction equation
[C:1]([CH2:3][C:4]([NH2:6])=[NH:5])#[N:2].Cl.C(CC(=N)OCC)#N.Br[CH:17]([CH3:27])[C:18]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[F:26])=O.O>C(O)C>[NH2:5][C:4]1[NH:6][C:18]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[F:26])=[C:17]([CH3:27])[C:3]=1[C:1]#[N:2]

Participants

6

Reactant 4

HCID 962WaterHCID 12342543Ethyl 2-cyanoacetimidate hydrochlorideHCID 220564242-CyanoacetimidamideHCID 221113342-Bromo-1-(2-fluorophenyl)propan-1-one

Product 1

HCID 101767492-amino-5-(2-fluorophenyl)-4-methyl-1H-pyrrole-3-carbonitrile

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To an ethanolic solution of 2-cyanoacetamidine prepared from 10 g of ethyl 2-cyanoacetimidate hydrochloride as in Reference Example 2 was added a solution of 2-bromo-2′-fluoropropiophenone (7.6 g) in ethanol dropwise under ice-cooling with stirring, and the mixture was then stirred at room temperature overnight. This reaction mixture was poured into iced water (500 g) and the resulting crystals were collected by filtration. The crude crystal crop was washed well with n-hexane, air-dried, and purified by flash chromatography (Kieselgel 60H, 90 g; eluent: 30% ethyl acetate/n-hexane). Recrystallization from benzene-n-hexane (1:1) yielded the title compound as colorless crystals (4.67 g). The physical constants of this product were in agreement with those of the product obtained in Example 5-(1).

Workup

  1. temperaturecooling
  2. stirringthe mixture was then stirred at room temperature overnight
  3. filtrationthe resulting crystals were collected by filtration
  4. washThe crude crystal crop was washed well with n-hexane
  5. customair-dried
  6. custompurified by flash chromatography (Kieselgel 60H, 90 g; eluent: 30% ethyl acetate/n-hexane)
  7. customRecrystallization from benzene-n-hexane (1:1)

Sources & evidence

ORD record
ord-d98dc504cdee462383049601db9d2a99
Source dataset
uspto-grants-2001_01
Patent number
US06172102B2

Reaction notes

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