Triphenylphosphine → 5-Bromo-6-(1-methyl-1H-imidazol-2-ylmethoxy)-nicotinic acid methyl ester

HRID 1929877Notes

Reaction equation

HRID 1929877 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[N:7][C:8]([OH:12])=[C:9]([Br:11])[CH:10]=1)=[O:4].[CH3:13][N:14]1[CH:18]=[CH:17][N:16]=[C:15]1[CH2:19]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(OC(N=NC(OC(C)C)=O)=O)(C)C>O1CCCC1>[CH3:1][O:2][C:3](=[O:4])[C:5]1[CH:10]=[C:9]([Br:11])[C:8]([O:12][CH2:19][C:15]2[N:14]([CH3:13])[CH:18]=[CH:17][N:16]=2)=[N:7][CH:6]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 573612(1-methyl-1H-imidazol-2-yl)methanolHCID 2764315Methyl 5-bromo-6-hydroxynicotinate

Product 1

HCID 675048445-Bromo-6-(1-methyl-1H-imidazol-2-ylmethoxy)-nicotinic acid methyl esterYield 27.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5-Bromo-6-hydroxy-3-pyridinecarboxylic acid methyl ester (1.0 g, 4.3 mmol) was suspended in tetrahydrofurane, 1-methyl-1H-imidazole-2-methanol (0.72 g, 6.5 mmol) and triphenylphosphine was added (1.70 g, 6.5 mmol). To this mixture was added with stirring diisopropyl-azodicarboxylate (1.35 mL, 6.5 mmol) at room temperature. Stirring was continued for 1 h at room temperature, solvent was removed and the residue was purified by chromatography with heptane/ethylacetate/methanol on silica gel to yield 0.38 g of the title compound as a colorless solid, MS (ISP) 326.0, 328.0 (M+H)−.

Workup

  1. customsolvent was removed
  2. customthe residue was purified by chromatography with heptane/ethylacetate/methanol on silica gel

Sources & evidence

ORD record
ord-c8f50967a3e84d31871a381e94e85b6e
Source dataset
uspto-grants-2012_05
Patent number
US08188093B2

Reaction notes

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