Water → 2-Methyl-6-[3-(1-pyridin-2-ylpiperidin-4-ylidene)prop-1-yn-1-yl]pyridine

HRID 1895970Notes

Reaction equation

HRID 1895970 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]#[C:9][CH:10]=[C:11]2[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)[N:3]=1.F[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=1.O>CN1CCCC1=O>[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]#[C:9][CH:10]=[C:11]2[CH2:12][CH2:13][N:14]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=3)[CH2:15][CH2:16]2)[N:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 97462-FluoropyridineHCID 875504022-Methyl-6-(3-piperidin-4-ylideneprop-1-ynyl)pyridine

Product 1

HCID 251816392-Methyl-6-[3-(1-pyridin-2-ylpiperidin-4-ylidene)prop-1-yn-1-yl]pyridineYield 14.7%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A solution of the Compound of Example 3 (100 mg, 0.47 mmol), 2-fluoropyridine (45.5 μL, 0.52 mmol), TEA (102 μL) in N-methylpyrrolidone was heated in a microwave oven at 160° C. for 20 min. Afterwards, the reaction mixture was cooled, poured into water and extracted with EtOAc. The combined organic layers were washed with brine, dried on Na2SO4 and evaporated to dryness in vacuo to afford a residue, which was purified by flash chromatography (EtOAc—Petroleum Ether gradient from 7:93 to 40:60) affording the title product (0.02 g).

Workup

  1. temperatureAfterwards, the reaction mixture was cooled
  2. extractionextracted with EtOAc
  3. washThe combined organic layers were washed with brine
  4. customdried on Na2SO4
  5. customevaporated to dryness in vacuo
  6. customto afford a residue, which
  7. customwas purified by flash chromatography (EtOAc—Petroleum Ether gradient from 7:93 to 40:60)

Sources & evidence

ORD record
ord-4c80cd0b669c4ed897450f978824b8e0
Source dataset
uspto-grants-2013_08
Patent number
US08518916B2

Reaction notes

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