HCID 89656225, compound → HCID 89655848, compound

HRID 626156Notes

Reaction equation

HRID 626156 reaction equation
[CH3:1][N:2]([CH3:22])[CH2:3][C:4]#[C:5][C:6]1[N:11]=[CH:10][C:9]([C:12]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)=[O:13])=[CH:8][CH:7]=1>[Ni].CO>[CH3:22][N:2]([CH3:1])[CH2:3][CH2:4][CH2:5][C:6]1[N:11]=[CH:10][C:9]([C:12]([C:14]2[CH:15]=[CH:16][C:17]([O:20][CH3:21])=[CH:18][CH:19]=2)=[O:13])=[CH:8][CH:7]=1

Participants

4

Reactant 1

HCID 89656225HCID 89656225, compound

Product 1

HCID 89655848HCID 89655848, compoundYield 95.2%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A flask was charged with (6-(3-(dimethylamino)prop-1-ynyl)pyridin-3-yl)-(4-methoxyphenyl)methanone (294 mg, 1 mmol) and Riney Ni (0.2 eq), and 20 mL methanol. The mixture was stirred under hydrogen at room temperature and atmospheric pressure for 2 h. The catalyst was filtered off through a pad of celite, washed with EtOAc. The filtrate was concentrated under reduced pressure to give the product (284 mg, 95% yield).

Workup

  1. filtrationThe catalyst was filtered off through a pad of celite
  2. washwashed with EtOAc
  3. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-962940ebad4f4fd1bfe008f9a56d468d
Source dataset
uspto-grants-2016_04
Patent number
US09309211B2

Reaction notes

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