18-Crown-6 → HCID 86710438, compound

HRID 1398465Notes

Reaction equation

HRID 1398465 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][C:13]=3F)[C:8](=[O:16])[N:7]([CH3:17])[C:6]=2[CH:18]=1.C1OCCOCCOCCOCCOCC[O:21][CH2:20]1.C[O-].[Na+]>CO.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:14]3[C:9](=[CH:10][N:11]=[CH:12][C:13]=3[O:21][CH3:20])[C:8](=[O:16])[N:7]([CH3:17])[C:6]=2[CH:18]=1

Participants

6

Reactant 3

HCID 2855718-Crown-6HCID 10942334Sodium MethoxideHCID 86710439HCID 86710439, compound

Product 1

HCID 86710438HCID 86710438, compoundYield 973.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

To the solution of 8-chloro-1-fluoro-6-methylbenzo[c][2,7]naphthyridin-5(6H)-one (40 mg, 0.152 mmol), prepared as described in Example 85, Part E, in MeOH (0.2 mL) in a microwave vial, 18-crown-6 (4.03 mg, 0.015 mmol) and sodium methoxide (32.9 mg, 0.152 mmol) in methanol were added and heated in a microwave oven at 100° C. for 30 min. Upon completion, the reaction mixture was diluted with water and extracted with ethyl acetate (2×5 mL). The combined organic layers were washed with brine solution, dried over sodium sulfate, filtered and concentrated under reduced pressure to afford 8-chloro-1-methoxy-6-methylbenzo[c][2,7]naphthyridin-5(6H)-one (40 mg, 0.146 mmol, 96% crude yield) as a white solid. The material was carried forward without further purification. LC/MS (ESI) m/e 275.0 [(M+H)+, calcd for C14H12ClN2O2 275.05]; LC/MS retention time (method D): tR=0.72 min.

Workup

  1. additionwere added
  2. extractionextracted with ethyl acetate (2×5 mL)
  3. washThe combined organic layers were washed with brine solution
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-fddc943039f74834a755fc5f1f6d0f33
Source dataset
uspto-grants-2014_12
Patent number
US08901305B2

Reaction notes

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