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

HRID 1845673Notes

Reaction equation

HRID 1845673 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)=[CH:22][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)=[CH:22][CH:21]=[N:20]1)[CH3:18]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 12239443Methyl 4-bromofuran-2-carboxylateHCID 532172521-Ethylpyrazole-5-boronic acid, pinacol ester

Product 1

HCID 57826888methyl 4-(1-ethyl-1H-pyrazol-5-yl)-2-furancarboxylateYield 74.5%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of methyl 4-bromo-2-furancarboxylate (1.0 g, 4.88 mmol) in THF (20 mL) was added aqueous Na2CO3 (2N, 8 mL, 16 mmol.), PdCl2(dppf) (0.35 g, 0.49 mmol) and 1-ethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (1.3 g, 5.85 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 (0.8 g, 74.5%) as a light yellow solid: LC-MS (ES) m/z=221 (M+H)+.

Workup

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

Sources & evidence

ORD record
ord-c5c31afa9ec643fa913915c48669c0ba
Source dataset
uspto-grants-2015_02
Patent number
US08946278B2

Reaction notes

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