1,2-Dibromoethane → (2,3-Dihydro-[1,4]dioxino[2,3-c]pyridin-7-yl)methanol

HRID 734223

Reaction equation

HRID 734223 reaction equation
[CH2:1]([O:8][C:9]1[C:10](=[O:17])[CH:11]=[C:12]([CH2:15][OH:16])[NH:13][CH:14]=1)[C:2]1C=CC=CC=1.[OH-].[Na+].C(=O)([O-])[O-].[K+].[K+].BrCCBr>O.[Pd].CN(C)C=O>[O:17]1[C:10]2[CH:11]=[C:12]([CH2:15][OH:16])[N:13]=[CH:14][C:9]=2[O:8][CH2:1][CH2:2]1

Participants

8

Reactant 4

HCID 78391,2-DibromoethaneHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 28015645-(Benzyloxy)-2-(hydroxymethyl)-1,4-dihydropyridin-4-one

Product 1

HCID 21873770(2,3-Dihydro-[1,4]dioxino[2,3-c]pyridin-7-yl)methanol

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
85 °C

Procedure

A solution of 5-benzyloxy-2-hydroxymethyl-1H-pyridin-4-one (2 g, 8.7 mmol) in water (220 mL) containing sodium hydroxide (17 mmol) was hydrogenated over 10% palladium on charcoal (1 g) for 4 hours. The mixture was filtered and evaporated to give a white solid. This solid was dissolved in N,N-dimethylformamide (8 mL) then treated with potassium carbonate (2.9 g) and 1,2-dibromoethane (0.6 mL, 7 mmol). The mixture was heated at 85° C. overnight. The cooled mixture was evaporated onto silica and chromatographed eluting with 10-30% methanol in ethyl acetate affording a white solid (250 mg, 21%): MS (APCI+) m/z 168 (MH+).

Workup

  1. filtrationThe mixture was filtered
  2. customevaporated
  3. customto give a white solid
  4. customThe cooled mixture was evaporated onto silica
  5. customchromatographed
  6. washeluting with 10-30% methanol in ethyl acetate affording a white solid (250 mg, 21%)

Sources & evidence

ORD record
ord-1a5e4a291b2942e7a87674e437d33ac3
Source dataset
uspto-grants-2009_09
Patent number
US07592334B2

Linked notes

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