2-Fluoropyridine → N-[3-(2H-Benzimidazol-2-ylidene)-2,3-dihydro-1H-pyrazol-4-yl]pyridin-2-amine

HRID 1012110Notes

Reaction equation

HRID 1012110 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[C:14]([NH2:15])=[CH:13][NH:12][N:11]=1.F[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=1>>[NH:3]1[C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[N:1]=[C:2]1[C:10]1[C:14]([NH:15][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=2)=[CH:13][NH:12][N:11]=1

Participants

3

Reactant 2

HCID 97462-FluoropyridineHCID 178508052HCID 178508052, compound

Product 1

HCID 178420478N-[3-(2H-Benzimidazol-2-ylidene)-2,3-dihydro-1H-pyrazol-4-yl]pyridin-2-amineYield 5.8%

Conditions

Temperature
150 °C

Procedure

A mixture of 3-(1H-benzimidazol-2-yl)-1H-pyrazol-4-ylamine (150 mg, 0.75 mmol) and 2-fluoropyridine (0.26 ml, 3.0 mmol) was heated in the microwave at 150° C. and 100 W for 15 min. Petroleum ether was added and the solid formed collected by filtration. Recrystallisation from methanol gave [3-(1H-benzimidazol-2-yl)-1H-pyrazol-4-yl]-pyridin-2-yl-amine (12 mg). (LC/MS: Rt 0.91, [M+H]+ 277.00).

Workup

  1. customthe solid formed
  2. filtrationcollected by filtration
  3. customRecrystallisation from methanol

Sources & evidence

ORD record
ord-9ec182b558744181939bff438b0efd82
Source dataset
uspto-grants-2011_07
Patent number
US07977477B2

Reaction notes

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