Sodium hydride → HCID 178470058, compound

HRID 1770662Notes

Reaction equation

HRID 1770662 reaction equation
[C:1]([C:4]1[C:9]([NH:10][C:11](=[O:18])[CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:8][C:7]([C:19]([F:22])([F:21])[F:20])=[CH:6][N:5]=1)(=O)[CH3:2].[H-].[Na+]>C(O)C>[OH:18][C:11]1[C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:1]([CH3:2])[C:4]2[C:9](=[CH:8][C:7]([C:19]([F:22])([F:21])[F:20])=[CH:6][N:5]=2)[N:10]=1

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 86720175HCID 86720175, compound

Product 1

HCID 178470058HCID 178470058, compoundYield 82.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a cooled (ice water batch) suspension of ethyl 3-(2-acetyl-5-(trifluoromethyl)pyridin-3-ylamino)-3-oxopropanoate (1.35 g, 4.24 mmol, 1 eq.) in ethanol (15 ml) was added NaH (60% w/w suspension in oil, 0.19 g, 4.66 mmol, 1.1 eq.) portion wise. The reaction mixture was stirred at RT for 1 h. Then the reaction was quenched with water (20 ml) and ethanol was distilled off. The residue was acidified with 5M aq. HCl (pH˜4) and was extracted with EtOAc (3×100 ml). The combined organic layers were washed with brine (100 ml), dried over anhydrous Na2SO4 and evaporated to provide the crude product, which was triturated with DCM (2×30 ml) to yield ethyl 2-hydroxy-4-methyl-7-(trifluoromethyl)-1,5-naphthyridine-3-carboxylate (1.05 g, 3.50 mmol, 82%).

Workup

  1. temperatureTo a cooled
  2. customThen the reaction was quenched with water (20 ml) and ethanol
  3. distillationwas distilled off
  4. extractionwas extracted with EtOAc (3×100 ml)
  5. washThe combined organic layers were washed with brine (100 ml)
  6. dry with materialdried over anhydrous Na2SO4
  7. customevaporated
  8. customto provide the crude product, which
  9. customwas triturated with DCM (2×30 ml)

Sources & evidence

ORD record
ord-6e4c32522595499c81ce1df020975b6c
Source dataset
uspto-grants-2016_02
Patent number
US09248122B2

Reaction notes

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