Ethanol → Ethyl 5-bromo-6-methoxy-3-pyridineacetate

HRID 2204338Notes

Reaction equation

HRID 2204338 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:10][C:11]([OH:13])=[O:12])[CH:5]=[N:6][C:7]=1[O:8][CH3:9].[CH2:14]1CCC(N=C=NC2CCCCC2)C[CH2:15]1.CCO.O>C(Cl)Cl.CN(C1C=CN=CC=1)C.CCOC(C)=O>[CH2:14]([O:12][C:11](=[O:13])[CH2:10][C:4]1[CH:5]=[N:6][C:7]([O:8][CH3:9])=[C:2]([Br:1])[CH:3]=1)[CH3:15]

Participants

8

Reactant 4

HCID 702EthanolHCID 962WaterHCID 10868DicyclohexylcarbodiimideHCID 82664957(5-Bromo-6-methoxy-pyridin-3-yl)-acetic acid

Product 1

HCID 58539686Ethyl 5-bromo-6-methoxy-3-pyridineacetate

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (5-bromo-6-methoxy-pyridin-3-yl)-acetic acid (Step AN2) (400 mg, 1.6 mmol) in CH2Cl2 (0.8 mL) was added DCC (18 mg, 0.09 mmol), DMAP (one spatula) and EtOH (4.88 mmol) and the mixture was stirred at rt for 15 h. H2O and EtOAc were added and the phases were separated. The organic layer was washed with brine, dried (MgSO4), filtered and concentrated. The residue was purified by flash chromatography (heptane/EtOAc, 85:15→0:100). ESI-MS: tR=1.05 min, [M+H]+ 274.1/276.1 (LC-MS 1).

Workup

  1. customthe phases were separated
  2. washThe organic layer was washed with brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography (heptane/EtOAc, 85:15→0:100)

Sources & evidence

ORD record
ord-e281f292b66541d2b86b0fe3b9227c9d
Source dataset
uspto-grants-2016_06
Patent number
US09365576B2

Reaction notes

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