Methanol → methyl 4-bromo-3-(methyloxy)-5-(1-methyl-1H-pyrazol-5-yl)-2-thiophenecarboxylate

HRID 1845381Notes

Reaction equation

HRID 1845381 reaction equation
[Br:1][C:2]1[C:3]([OH:17])=[C:4]([C:13]([O:15][CH3:16])=[O:14])[S:5][C:6]=1[C:7]1[N:11]([CH3:12])[N:10]=[CH:9][CH:8]=1.CO.[CH:20]1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[Br:1][C:2]1[C:3]([O:17][CH3:20])=[C:4]([C:13]([O:15][CH3:16])=[O:14])[S:5][C:6]=1[C:7]1[N:11]([CH3:12])[N:10]=[CH:9][CH:8]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 57826681methyl 4-bromo-3-hydroxy-5-(1-methyl-1H-pyrazol-5-yl)-2-thiophenecarboxylate

Product 1

HCID 57826414methyl 4-bromo-3-(methyloxy)-5-(1-methyl-1H-pyrazol-5-yl)-2-thiophenecarboxylateYield 74%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 4-bromo-3-hydroxy-5-(1-methyl-1H-pyrazol-5-yl)-2-thiophenecarboxylate (175 mg, 0.554 mmol), MeOH (26 μL, 0.609 mmol), PPh3 (189 mg, 0.720 mmol) in THF (6 mL) at 25° C. was added DEAD (113 μL, 0.720 mmol) in one portion. After 30 min, the reaction was concentrated and purified via column chromatography (silica, 20% EtOAc in hexanes) affording the title compound (135 mg, 74%) as a white solid: LC-MS (ES) m/z=332 (M+H)+.

Workup

  1. concentrationthe reaction was concentrated
  2. custompurified via column chromatography (silica, 20% EtOAc in hexanes)

Sources & evidence

ORD record
ord-f45908f330bb4fa3b485b1d3a854a625
Source dataset
uspto-grants-2015_02
Patent number
US08946278B2

Reaction notes

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