Cesium carbonate → 6-(4-methoxybenzyl)-2-vinyl-7,8-dihydro-1,6-naphthyridin-5(6H)-one

HRID 533150Notes

Reaction equation

HRID 533150 reaction equation
Cl[C:2]1[CH:11]=[CH:10][C:9]2[C:8](=[O:12])[N:7]([CH2:13][C:14]3[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=3)[CH2:6][CH2:5][C:4]=2[N:3]=1.[CH:22]([B-](F)(F)F)=[CH2:23].[K+].C([O-])([O-])=O.[Cs+].[Cs+]>CCO.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:21][O:20][C:17]1[CH:18]=[CH:19][C:14]([CH2:13][N:7]2[CH2:6][CH2:5][C:4]3[N:3]=[C:2]([CH:22]=[CH2:23])[CH:11]=[CH:10][C:9]=3[C:8]2=[O:12])=[CH:15][CH:16]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 23679353Potassium vinyltrifluoroborateHCID 866675022-chloro-6-(4-methoxybenzyl)-7,8-dihydro-1,6-naphthyridin-5(6H)-one

Product 1

HCID 680080226-(4-methoxybenzyl)-2-vinyl-7,8-dihydro-1,6-naphthyridin-5(6H)-one

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolvent

Conditions

Temperature
150 °C

Procedure

2-chloro-6-(4-methoxybenzyl)-7,8-dihydro-1,6-naphthyridin-5(6H)-one, (1.5 g, 4.97 mmol) was dissolved in EtOH with potassium vinyltrifluoroborate (865 mg, 6.46 mmol), Cs2CO3 (2.42 g, 7.46 mmol) and Pd(PPh3)4 (115 mg, 0.01 mmol). The reaction was heated in a microwave synthesizer at 150° C. for 1 h. It was then concentrated and purified over silica gel (EtOAc/hexanes) to give after solvent removal and drying in vacuo the compound as an off-white solid (1.1 g, 76%). LC-MS (M+H)=295.2.

Workup

  1. concentrationIt was then concentrated
  2. custompurified over silica gel (EtOAc/hexanes)
  3. customto give
  4. customafter solvent removal
  5. dry with materialdrying in vacuo the compound as an off-white solid (1.1 g, 76%)

Sources & evidence

ORD record
ord-342ee0c5ba904e8880c8d1039abbf66f
Source dataset
uspto-grants-2014_10
Patent number
US08853237B2

Reaction notes

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