Potassium Phosphate, Tribasic → 2-(4-methylpyridin-3-yl)-3,4-dihydro-2,7-naphthyridin-1(2H)-one

HRID 1844006Notes

Reaction equation

HRID 1844006 reaction equation
[C:1]1(=[O:11])[C:10]2[C:5](=[CH:6][CH:7]=[N:8][CH:9]=2)[CH2:4][CH2:3][NH:2]1.I[C:13]1[CH:14]=[N:15][CH:16]=[CH:17][C:18]=1[CH3:19].P([O-])([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.[Cu](I)I>[CH3:19][C:18]1[CH:17]=[CH:16][N:15]=[CH:14][C:13]=1[N:2]1[CH2:3][CH2:4][C:5]2[C:10](=[CH:9][N:8]=[CH:7][CH:6]=2)[C:1]1=[O:11]

Participants

6

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 111826883,4-Dihydro-2,7-naphthyridin-1(2H)-oneHCID 144235133-Iodo-4-methylpyridine

Product 1

HCID 668073852-(4-methylpyridin-3-yl)-3,4-dihydro-2,7-naphthyridin-1(2H)-oneYield 12.4%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 312751,4-DioxaneSolvent

Procedure

3,4-Dihydro-2,7-naphthyridin-1(2H)-one (I-65f: 80 mg, 0.5399 mmol) was reacted with 3-iodo-4-methylpyridine (177 mg, 0.8099 mmol), copper iodide (8 mg, 10% w/w), trans-N,N′-dimethyl-cyclohexyl-1,2-diamine (16 mg, 20% w/w) and potassium phosphate (287 mg, 1.3498 mmol) in 1,4-dioxane (5 mL) to afford the crude product. Purification by column chromatography on silica gel (3% methanol in CHCl3), followed by preparative HPLC afforded 16 mg of the product (12.4% yield).

Workup

  1. customto afford the crude product
  2. customPurification by column chromatography on silica gel (3% methanol in CHCl3)

Sources & evidence

ORD record
ord-dcbe939378d341a09446c932450d900b
Source dataset
uspto-grants-2015_02
Patent number
US08946260B2

Reaction notes

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