Potassium Carbonate → ethyl 2-(3-(1-methyl-1H-pyrazol-5-yl)phenyl)acetate

HRID 1429481Notes

Reaction equation

HRID 1429481 reaction equation
CC1(C)C(C)(C)OB([C:9]2[CH:10]=[C:11]([CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH:12]=[CH:13][CH:14]=2)O1.Br[C:23]1[N:27]([CH3:28])[N:26]=[CH:25][CH:24]=1.C([O-])([O-])=O.[K+].[K+].O1CCOCC1>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].O>[CH3:28][N:27]1[C:23]([C:9]2[CH:10]=[C:11]([CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH:12]=[CH:13][CH:14]=2)=[CH:24][CH:25]=[N:26]1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 179333815-Bromo-1-methyl-1H-pyrazoleHCID 53217140Ethyl 2-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetate

Product 1

HCID 90241563ethyl 2-(3-(1-methyl-1H-pyrazol-5-yl)phenyl)acetateYield 70.4%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of ethyl 2-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetate (500 mg, 1.72 mmol), 5-bromo-1-methyl-1H-pyrazole (252 mg, 1.57 mmol), K2CO3 (651 mg, 4.71 mmol) and Pd(dppf)Cl2 (20 mg) in a solution of dioxane (10 mL) and H2O (2.5 mL) was stirred at 120° C. for 30 min under microwave. The catalyst was filtered through a pad of celite and the filtrate concentrated. The residue was purified by column chromatography to give the desired product (270 mg, Yield 70%) and used directly in the next step. LCMS (m/z): 245.1 (M+1).

Workup

  1. filtrationThe catalyst was filtered through a pad of celite
  2. concentrationthe filtrate concentrated
  3. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-3cb252d8132443479f4cfffe8eb85d4d
Source dataset
uspto-grants-2015_01
Patent number
US08940726B2

Reaction notes

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