Potassium Carbonate → methyl 4-(1,4-dimethyl-1H-pyrazol-5-yl)-5-methyl-2-thiophenecarboxylate

HRID 1961212Notes

Reaction equation

Br[C:2]1[CH:3]=[N:4][N:5]([CH3:17])[C:6]=1[C:7]1[CH:8]=[C:9]([C:13]([O:15][CH3:16])=[O:14])[S:10][C:11]=1[CH3:12].[CH3:18]B1OB(C)OB(C)O1.C([O-])([O-])=O.[K+].[K+]>CN(C)C=O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH3:17][N:5]1[C:6]([C:7]2[CH:8]=[C:9]([C:13]([O:15][CH3:16])=[O:14])[S:10][C:11]=2[CH3:12])=[C:2]([CH3:18])[CH:3]=[N:4]1

Participants

Conditions

Temperature: 110 °C

Procedure

To a 350 mL sealed flask reactor was added methyl 4-(4-bromo-1-methyl-1H-pyrazol-5-yl)-5-methyl-2-thiophenecarboxylate (2.57 g, 8.15 mmol), trimethylboroxine (2.27 ml, 16.31 mmol), K2CO3 (3.47 g, 25.1 mmol) and Pd(dppf)Cl2 (426 mg, 0.83 mmol) in N,N-Dimethylformamide (DMF) (41 ml). The reaction was heated at 110° C. for 1 hour. The mixture was partitioned between CHCl3/H2O, organic layer separated and dried with Na2SO4. The resulting material was adsorbed onto silica and purified via column chromatography (0-15% EtOAc/Hexane) affording the title compound (1.3 g, 4.76 mmol, 58%): LC-MS (ES) m/z=251 (M+H)+.

Workup

customTo a 350 mL sealed flask reactor
customThe mixture was partitioned between CHCl3/H2O, organic layer
customseparated
dry with materialdried with Na2SO4
custompurified via column chromatography (0-15% EtOAc/Hexane)

Sources & evidence

ORD record: ord-a4a39c9a034f49ef8e4dcdc0b8d221e8
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08410158B2

Reaction notes

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