(6-(3-(pyrrolidin-1-yl)prop-1-ynyl)pyridin-3-yl)(4-(tetrahydro-2H-pyran-2-yloxy)phenyl)methanone → (6-(3-(pyrrolidin-1-yl)propyl)pyridin-3-yl)(4-(tetrahydro-2H-pyran-2-yl-oxy)phenyl)methanone

HRID 626274Notes

Reaction equation

HRID 626274 reaction equation
[N:1]1([CH2:6][C:7]#[C:8][C:9]2[N:14]=[CH:13][C:12]([C:15]([C:17]3[CH:22]=[CH:21][C:20]([O:23][CH:24]4[CH2:29][CH2:28][CH2:27][CH2:26][O:25]4)=[CH:19][CH:18]=3)=[O:16])=[CH:11][CH:10]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1>[Ni].CO>[N:1]1([CH2:6][CH2:7][CH2:8][C:9]2[N:14]=[CH:13][C:12]([C:15]([C:17]3[CH:18]=[CH:19][C:20]([O:23][CH:24]4[CH2:29][CH2:28][CH2:27][CH2:26][O:25]4)=[CH:21][CH:22]=3)=[O:16])=[CH:11][CH:10]=2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

4

Reactant 1

HCID 89672880(6-(3-(pyrrolidin-1-yl)prop-1-ynyl)pyridin-3-yl)(4-(tetrahydro-2H-pyran-2-yloxy)phenyl)methanone

Product 1

HCID 89672867(6-(3-(pyrrolidin-1-yl)propyl)pyridin-3-yl)(4-(tetrahydro-2H-pyran-2-yl-oxy)phenyl)methanoneYield 77.3%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

Raney nickel (0.3 g, 0.6 mmol, 10 mol %) was added to the solution of (6-(3-(pyrrolidin-1-yl)prop-1-ynyl)pyridin-3-yl)(4-(tetrahydro-2H-pyran-2-yloxy)phenyl)methanone (2.2 g, 5.6 mmol) in 20 mL methanol at room temperature, and the reaction mixture was stirred for 1 h under hydrogen atmosphere. Filtered off the nickel and the filtrate was concentrated in vacuo to afford the desired product as a yellow solid (1.7 g, 77.3%).

Workup

  1. filtrationFiltered off the nickel
  2. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-b7831d09c6a14f16b0c8af4ef16b04f1
Source dataset
uspto-grants-2016_04
Patent number
US09309211B2

Reaction notes

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