Dichloromethane → HCID 117667217, compound

HRID 712618Notes

Reaction equation

HRID 712618 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:17]2[C:12](=[CH:13][C:14]([Br:18])=[CH:15][N:16]=2)[CH2:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[O-:19]S([O-])=O.[Na+].[Na+].CCOC(C)=O.C(Cl)Cl>C(O)(C)(C)C.O>[C:1]([O:5][C:6]([N:8]1[C:17]2[C:12](=[CH:13][C:14]([Br:18])=[CH:15][N:16]=2)[C:11](=[O:19])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 8857Ethyl AcetateHCID 24437Sodium SulfiteHCID 11833959tert-Butyl 6-bromo-3,4-dihydro-1,8-naphthyridine-1(2H)-carboxylate

Product 1

HCID 117667217HCID 117667217, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6386tert-ButanolSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 6-bromo-3,4-dihydro-2H-[1,8]naphthyridine-1-carboxylic acid tert-butyl ester (2.16 g, 6.90 mmol) and NaH2PO4 (2.38 g, 17.2 mmol) in t-butanol and water (1:1 mixture, 300 mL) is heated to 50° C. and NaMnO4 (11.4 g, 32.2 mmol) solution (aq.) is added. The mixture is heated for 2 hrs. The reaction mixture is cooled and solid Na2SO3 is added until the purple color disappears. 50 mL of EtOAc and 50 mL of water are added and the mixture is filtered through diatomaceous earth to remove the black solid. The aqueous layer of the filtrate is separated and extracted with 2×100 mL of EtOAc. The organic layers are combined dried with MgSO4 and concentrated to give the crude product. The product is dissolved into CH2Cl2 and purified via silica chromatography to give 1.09 g 6-bromo-4-oxo-3,4-dihydro-2H-[1,8]naphthyridine-1-carboxylic acid tert-butyl ester.

Workup

  1. temperatureThe mixture is heated for 2 hrs
  2. temperatureThe reaction mixture is cooled
  3. filtrationthe mixture is filtered through diatomaceous earth
  4. customto remove the black solid
  5. customThe aqueous layer of the filtrate is separated
  6. extractionextracted with 2×100 mL of EtOAc
  7. dry with materialThe organic layers are combined dried with MgSO4
  8. concentrationconcentrated
  9. customto give the crude product
  10. custompurified via silica chromatography

Sources & evidence

ORD record
ord-a24e9e5ad58f496ba982af06fd7f8a4e
Source dataset
uspto-grants-2015_11
Patent number
US09181272B2

Reaction notes

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