Ethyl bromoacetate → (6-Methoxy-[1,5]naphthyridin-4-yloxy)-acetic acid

HRID 1640544Notes

Reaction equation

HRID 1640544 reaction equation
C([O-])([O-])=O.[K+].[K+].[CH3:7][O:8][C:9]1[N:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[N:15]=[CH:14][CH:13]=[C:12]2[OH:19].Br[CH2:21][C:22]([O:24]CC)=[O:23].[OH-].[Na+]>CS(C)=O>[CH3:7][O:8][C:9]1[N:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[N:15]=[CH:14][CH:13]=[C:12]2[O:19][CH2:21][C:22]([OH:24])=[O:23]

Participants

6

Reactant 4

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 178487891HCID 178487891, compound

Product 1

HCID 66737291(6-Methoxy-[1,5]naphthyridin-4-yloxy)-acetic acidYield 52%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
50 °C

Procedure

K2CO3 (785 mg, 1 eq.) was added to a suspension of 6-methoxy-[1,5]naphthyridin-4-ol (1 g, 5.7 mmol, WO 02/08224) in DMSO (7 mL). The mixture was vigorously stirred for 2.5 h after which ethyl bromoacetate was added dropwise. The resulting mixture was heated at 50° C. for 4 h. 2N NaOH (5 mL) was then added at 50° C. and stirring was continued at rt overnight. The mixture was quenched with water. AcOH was added and the mixture was extracted with DCM/MeOH 9:1. The org. layer was washed with water, dried over MgSO4 and concentrated to afford the title intermediate as a pale yellow solid (693 mg, 52% yield).

Workup

  1. additionwas added dropwise
  2. customThe mixture was quenched with water
  3. additionAcOH was added
  4. extractionthe mixture was extracted with DCM/MeOH 9:1
  5. washlayer was washed with water
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-f9a63daa3dfc4bc6aafcc8a4de82d92e
Source dataset
uspto-grants-2012_02
Patent number
US08114867B2

Reaction notes

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