6-Fluoropyridin-2-amine → HCID 80648332, compound

HRID 1755340Notes

Reaction equation

HRID 1755340 reaction equation
F[C:2]1[N:7]=[C:6]([NH2:8])[CH:5]=[CH:4][CH:3]=1.[CH2:9]([CH:11]1[CH2:15][CH2:14][CH2:13][NH:12]1)[CH3:10]>O>[CH2:9]([CH:11]1[CH2:15][CH2:14][CH2:13][N:12]1[C:2]1[N:7]=[C:6]([NH2:8])[CH:5]=[CH:4][CH:3]=1)[CH3:10]

Participants

4

Reactant 2

HCID 27613996-Fluoropyridin-2-amineHCID 49934652-Ethylpyrrolidine

Product 1

HCID 80648332HCID 80648332, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
205 °C

Procedure

A mixture of 6-fluoropyridin-2-amine (0.5 g, 4.46 mmol) and 2-ethylpyrrolidine (0.664 g, 6.7 mmol) in water (0.3 mL) was heated to 205° C. for 0.5 h in a microwave oven then concentrated in vacuo. The residue was purified by chromatography (silica gel, 10 g, 200˜300 mesh, ethyl acetate:petroleum ether=1:30) to afford 6-(2-ethylpyrrolidin-1-yl)pyridin-2-amine (0.57 g, 67%) as a yellow oil. LC-MS: [M+1]+=192, tR=1.100 min.

Workup

  1. concentrationthen concentrated in vacuo
  2. customThe residue was purified by chromatography (silica gel, 10 g, 200˜300 mesh, ethyl acetate:petroleum ether=1:30)

Sources & evidence

ORD record
ord-3e3aff2091e04ffea0e89be9050fa964
Source dataset
uspto-grants-2015_10
Patent number
US09169259B2

Reaction notes

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