Dichloromethane → 6-(3-fluorophenyl)-7,8-dihydro-1,6-naphthyridin-5(6H)-one

HRID 533148Notes

Reaction equation

HRID 533148 reaction equation
FC1C=C(C=CC=1)CO[C:7]1[CH:16]=[CH:15][C:14]2[C:13](=[O:17])[NH:12][CH2:11][CH2:10][C:9]=2[N:8]=1.C(Cl)Cl.[F:24][C:25]1[CH:26]=[C:27](B(O)O)[CH:28]=[CH:29][CH:30]=1>CC([O-])=O.CC([O-])=O.[Cu+2].C(N(CC)CC)C>[F:24][C:25]1[CH:30]=[C:29]([N:12]2[CH2:11][CH2:10][C:9]3[N:8]=[CH:7][CH:16]=[CH:15][C:14]=3[C:13]2=[O:17])[CH:28]=[CH:27][CH:26]=1

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 27339863-Fluorophenylboronic acidHCID 574052642-((3-fluorobenzyl)oxy)-7,8-dihydro-1,6-naphthyridin-5(6H)-one

Product 1

HCID 866675036-(3-fluorophenyl)-7,8-dihydro-1,6-naphthyridin-5(6H)-one

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 8471TriethylamineSolvent

Procedure

2-((3-fluorobenzyl)oxy)-7,8-dihydro-1,6-naphthyridin-5(6H)-one (30 mg, 0.11 mmol) was dissolved into DCM (2 mL) and treated with 3-fluorophenylboronic acid (30 mg, 0.22 mmol), Cu(OAc)2 (22 mg, 0.13 mmol), and triethylamine (50 μL). The reaction was stirred for 2 days at RT and concentrated to an oil and purified by RP-HPLC (10-90% gradient CH3CN in water with 0.1% TFA modifier) to give the compound, 24(3-fluorobenzyl)oxy)-6-(3-fluorophenyl)-7,8-dihydro-1,6-naphthyridin-5(6H)-one. LC-MS (M+H)=367.2.

Workup

  1. concentrationconcentrated to an oil
  2. custompurified by RP-HPLC (10-90% gradient CH3CN in water with 0.1% TFA modifier)

Sources & evidence

ORD record
ord-e90650fda1bd45efaa3dbc806dce30bc
Source dataset
uspto-grants-2014_10
Patent number
US08853237B2

Reaction notes

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