Sodium Carbonate → methyl 4-(1-ethyl-4-methyl-1H-pyrazol-5-yl)-2-furancarboxylate

HRID 1845671Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]([C:7]([O:9][CH3:10])=[O:8])[O:5][CH:6]=1.C([O-])([O-])=O.[Na+].[Na+].[CH2:17]([N:19]1[C:23](B2OC(C)(C)C(C)(C)O2)=[C:22]([CH3:33])[CH:21]=[N:20]1)[CH3:18]>C1COCC1.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]>[CH2:17]([N:19]1[C:23]([C:2]2[CH:3]=[C:4]([C:7]([O:9][CH3:10])=[O:8])[O:5][CH:6]=2)=[C:22]([CH3:33])[CH:21]=[N:20]1)[CH3:18]

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of methyl 4-bromo-2-furancarboxylate (500 mg, 2.439 mmol) in THF (5 mL) was added aqueous Na2CO3 (2N, 3.6 mL, 7.2 mmol), PdCl2(dppf) (160 mg, 0.22 mmol), and 1-ethyl-4-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (700 mg, 2.96 mmol). The reaction mixture was heated to 70° C. in a sealed tube. After 2 h, the reaction mixture was concentrated under vacuum and purified on silica (EtOAc/Hex, 20-40%) to afford the title compound (460 mg, 76%) as a light yellow solid: LC-MS (ES) m/z 235 (M+H)+.

Workup

concentrationthe reaction mixture was concentrated under vacuum
custompurified on silica (EtOAc/Hex, 20-40%)

Sources & evidence

ORD record: ord-046c0ce16817466f87a17f767696542f
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08946278B2

Reaction notes

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