2-Methoxyethanol → 5-Bromo-6-(2-methoxy-ethoxy)-nicotinic acid methyl ester

HRID 1929801Notes

Reaction equation

HRID 1929801 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[C:9]([Br:11])[C:8](=[O:12])[NH:7][CH:6]=1)=[O:4].[CH3:13][O:14][CH2:15][CH2:16]O.CC(OC(/N=N/C(OC(C)C)=O)=O)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[CH3:1][O:2][C:3](=[O:4])[C:5]1[CH:10]=[C:9]([Br:11])[C:8]([O:12][CH2:16][CH2:15][O:14][CH3:13])=[N:7][CH:6]=1

Participants

6

Reactant 4

HCID 80192-MethoxyethanolHCID 11776TriphenylphosphineHCID 2764315Methyl 5-bromo-6-hydroxynicotinateHCID 5363146Diisopropyl azodicarboxylate

Product 1

HCID 675049645-Bromo-6-(2-methoxy-ethoxy)-nicotinic acid methyl esterYield 45.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5-Bromo-1,6-dihydro-6-oxo-3-pyridinecarboxylic acid methyl ester (15 g, 65 mmol, CA 381247-99-0) was suspended in THF (500 mL). To this suspension was added with stirring 2-methoxyethanol (7.1 mL, 97 mmol), diisopropylazodicarboxylate (21.5 mL, 97 mmol) and triphenylphosphine (25.4 g, 97 mmol). This mixture was stirred for 1 h at room temperature and the solvent was removed in vacuo. The residue was purified by flash chromatography on silica (heptane/ethylacetate, 2:1) to give the title compound (8.65 g) as a yellow solid; MS (ISP) 290.1 (M+H)+.

Workup

  1. customthe solvent was removed in vacuo
  2. customThe residue was purified by flash chromatography on silica (heptane/ethylacetate, 2:1)

Sources & evidence

ORD record
ord-d70b02c9e02a425f87ab8c4aac218051
Source dataset
uspto-grants-2012_05
Patent number
US08188093B2

Reaction notes

Loading…