1,2-Dibromoethane → Methyl 2,3-dihydro[1,4]dioxino[2,3-c]pyridine-7-carboxylate

HRID 965834Notes

Reaction equation

HRID 965834 reaction equation
[OH:1][C:2]1[C:7]([OH:8])=[CH:6][N:5]=[C:4]([C:9]([O:11][CH3:12])=[O:10])[CH:3]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:20][CH2:21]Br>CN(C=O)C>[O:1]1[C:2]2[CH:3]=[C:4]([C:9]([O:11][CH3:12])=[O:10])[N:5]=[CH:6][C:7]=2[O:8][CH2:21][CH2:20]1

Participants

5

Reactant 3

HCID 78391,2-DibromoethaneHCID 11430Potassium CarbonateHCID 178498577HCID 178498577, compound

Product 1

HCID 22313340Methyl 2,3-dihydro[1,4]dioxino[2,3-c]pyridine-7-carboxylateYield 86.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
115 °C

Procedure

To a stirred solution of methyl 4,5-dihydroxypyridine-2-carboxylate (348 mg, 2.06 mmol) in DMF (20 mL) is added solid K2CO3 (3.1 g, 22 mmol) and 1,2-dibromoethane (386 μL, 4.5 mmol). The mixture is heated at 115° C. for 2 h. DMF is removed in vacuo, the residue is partitioned between water and EtOAc. The aqueous layer is again extracted with EtOAc. The combined organic layers are dried (MgSO4) and concentrated in vacuo to give a yellow solid for methyl 2,3-dihydro-1,4-dioxino[2,3-c]pyridine-7-carboxylate (348 mg, 86%): 1H NMR (400 MHz, CDCl3) δ 8.29, 7.71, 4.39, 3.99.

Workup

  1. customDMF is removed in vacuo
  2. customthe residue is partitioned between water and EtOAc
  3. extractionThe aqueous layer is again extracted with EtOAc
  4. dry with materialThe combined organic layers are dried (MgSO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1429a21d767b4e7da2d854ff6ec80519
Source dataset
uspto-grants-2005_10
Patent number
US06951868B2

Reaction notes

Loading…