(E)-2-Methoxy-4-(2-(pyridin-2-yl)vinyl)pyridine → 2-Methoxy-4-(2-(pyridin-2-yl)ethyl)pyridine

HRID 2387518Notes

Reaction equation

HRID 2387518 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7](/[CH:9]=[CH:10]/[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=2)[CH:6]=[CH:5][N:4]=1>CO>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH2:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=2)[CH:6]=[CH:5][N:4]=1

Participants

3

Reactant 1

HCID 59293390(E)-2-Methoxy-4-(2-(pyridin-2-yl)vinyl)pyridine

Product 1

HCID 592934092-Methoxy-4-(2-(pyridin-2-yl)ethyl)pyridineYield 718%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(E)-2-Methoxy-4-(2-(pyridin-2-yl)vinyl)pyridine (290 mg, 0.13 mmol) was dissolved in MeOH (15 mL) and degassed with a nitrogen stream for 10 minutes. Palladium on charcoal (10%, wet, 5 g) was added and the reaction mixture stirred under an atmosphere of hydrogen for 24 h. The reaction mixture was degassed again and the catalyst removed by filtration. Concentration of the filtrate provided the title compound (200 mg, 90%) as a green oil: 1H NMR (500 MHz, CD3OD) δ 8.56 (d, J=5.1 Hz, 1H), 8.03 (d, J=5.1 Hz, 1H), 7.59-7.55 (dt, J=7.9, 19 Hz, 1H), 7.14-7.10 (dd, J=7.2, 5.1 Hz, 1H), 7.08 (d, J=7.6 Hz, 1H), 6.71 (d, J=5.4 Hz, 1H), 6.56 (s, 1H), 3.90 (s, 3H), 3.10-3.06 (m, 2H), 3.04-3.00 (m, 2H).

Workup

  1. customdegassed with a nitrogen stream for 10 minutes
  2. additionPalladium on charcoal (10%, wet, 5 g) was added
  3. customThe reaction mixture was degassed again
  4. customthe catalyst removed by filtration

Sources & evidence

ORD record
ord-5dec5d5f67754e02bfd610547381799e
Source dataset
uspto-grants-2012_09
Patent number
US08268868B2

Reaction notes

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