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

HRID 2233339Notes

Reaction equation

HRID 2233339 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]>[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

7

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)methanolYield 17.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Conditions

Temperature
85 °C

Procedure

A solution of 5-benzyloxy-2-(hydroxymethyl)-4(1H)-pyridinone (2 g, 8.7 mmole) and NaOH (680 mg, 17 mmole) in water (220 mL) was hydrogenated over 10% palladium on charcoal (1 g). After 4 hr, the mixture was filtered and the filtrate was concentrated to dryness. The resulting white solid was dissolved in DMF (8 mL) then treated with potassium carbonate (2.9 g, 21 mmole) and 1,2-dibromoethane (0.6 mL, 7 mmole). The mixture was heated at 85° C. overnight. The cooled mixture was concentrated onto silica gel and chromatographed (gradient elution: 10-30% MeOH/EtOAc) to afford the title compound (250 mg, 17%) as a white solid: MS (APCI+) m/e 168 (M+H)+.

Workup

  1. filtrationthe mixture was filtered
  2. concentrationthe filtrate was concentrated to dryness
  3. dissolutionThe resulting white solid was dissolved in DMF (8 mL)
  4. concentrationThe cooled mixture was concentrated onto silica gel
  5. customchromatographed
  6. wash(gradient elution: 10-30% MeOH/EtOAc)

Sources & evidence

ORD record
ord-277702047b4e4a05b9c80bacbbbf4004
Source dataset
uspto-grants-2010_05
Patent number
US07709496B2

Reaction notes

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