2-Bromoethyl methyl ether → 8-chloro-6-(2-methoxyethyl)benzo[c][2,7]naphthyridin-5(6H)-one

HRID 1398317Notes

Reaction equation

HRID 1398317 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:14]3[C:9](=[CH:10][N:11]=[CH:12][CH:13]=3)[C:8](=[O:15])[NH:7][C:6]=2[CH:16]=1.[CH3:17][O:18][CH2:19][CH2:20]Br>CN(C=O)C.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:14]3[C:9](=[CH:10][N:11]=[CH:12][CH:13]=3)[C:8](=[O:15])[N:7]([CH2:20][CH2:19][O:18][CH3:17])[C:6]=2[CH:16]=1

Participants

5

Reactant 2

HCID 809722-Bromoethyl methyl etherHCID 867103228-chlorobenzo[c][2,7]naphthyridin-5(6H)-one

Product 1

HCID 867103238-chloro-6-(2-methoxyethyl)benzo[c][2,7]naphthyridin-5(6H)-oneYield 80%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 8-chlorobenzo[c][2,7]naphthyridin-5(6H)-one (0.150 g, 0.650 mmol) in anhydrous DMF (2 mL) at 0° C. was added 2-bromoethyl methyl ether (0.090 g, 0.650 mmol) under nitrogen. The reaction mixture was allowed to warm to RT and stirred for 12 h. The reaction mixture was diluted with water (10 mL) and extracted with ethyl acetate (2×20 mL). The combined organic layers were dried over sodium sulfate and concentrated under reduced pressure to afford 8-chloro-6-(2-methoxyethyl)benzo[c][2,7]naphthyridin-5(6H)-one (150 mg, 0.520 mmol, 80% yield). LC/MS (ESI) m/e 289.1 [(M+H)+, calcd for C15H13ClN2O2 289.1]; LC/MS retention time (method A): tR=1.65 min.

Workup

  1. extractionextracted with ethyl acetate (2×20 mL)
  2. dry with materialThe combined organic layers were dried over sodium sulfate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-72f02d53262f4894a0f82d9abdade913
Source dataset
uspto-grants-2014_12
Patent number
US08901305B2

Reaction notes

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