Methanol → 2-(4-methoxybenzyl)-3,4-dihydro-2,7-naphthyridin-1(2H)-one

HRID 1844004Notes

Reaction equation

HRID 1844004 reaction equation
CCOC(/N=N/C(OCC)=O)=O.O[CH2:14][CH2:15][C:16]1[C:21]([C:22]([NH:24][CH2:25][C:26]2[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=2)=[O:23])=[CH:20][N:19]=[CH:18][CH:17]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CO>C1COCC1.C(Cl)(Cl)Cl>[CH3:33][O:32][C:29]1[CH:30]=[CH:31][C:26]([CH2:25][N:24]2[CH2:14][CH2:15][C:16]3[C:21](=[CH:20][N:19]=[CH:18][CH:17]=3)[C:22]2=[O:23])=[CH:27][CH:28]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 668036304-(2-hydroxyethyl)-N-(4-methoxybenzyl)nicotinamide

Product 1

HCID 112886342-(4-methoxybenzyl)-3,4-dihydro-2,7-naphthyridin-1(2H)-oneYield 49.82%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8028TetrahydrofuranSolvent

Procedure

DEAD (1.094 g, 6.286 mmol) was added drop wise to a solution of 4-(2-hydroxyethyl)-N-(4-methoxybenzyl)nicotinamide (I-65d: 1.5 g, 5.238 mmol) and PPh3 (2.784 g, 10.477 mmol) in THF (40 mL) at 0° C. and the resulting reaction mass was stirred at room temperature for 1 hour. The reaction was monitored by TLC (10% methanol in CHCl3). The reaction mass was concentrated under reduced pressure and the crude residue was purified by column chromatography on silica gel (3% methanol in DCM) to afford 700 mg of the product (49.82% yield).

Workup

  1. customthe resulting reaction mass
  2. concentrationThe reaction mass was concentrated under reduced pressure
  3. customthe crude residue was purified by column chromatography on silica gel (3% methanol in DCM)

Sources & evidence

ORD record
ord-eae0d287df6e42b8a05111af28ca3d4d
Source dataset
uspto-grants-2015_02
Patent number
US08946260B2

Reaction notes

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