Potassium Carbonate → 6-Cyclopentenyl-pyridine-2-carboxylic acid

HRID 632112

Reaction equation

HRID 632112 reaction equation
Br[C:2]1[N:7]=[C:6]([C:8]([OH:10])=[O:9])[CH:5]=[CH:4][CH:3]=1.[C:11]1(B2OC(C)(C)C(C)(C)O2)[CH2:15][CH2:14][CH2:13][CH:12]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)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]>[C:11]1([C:2]2[N:7]=[C:6]([C:8]([OH:10])=[O:9])[CH:5]=[CH:4][CH:3]=2)[CH2:15][CH2:14][CH2:13][CH:12]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 5939196-Bromopyridine-2-carboxylic acidHCID 154866112-(Cyclopent-1-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Product 1

HCID 866747586-Cyclopentenyl-pyridine-2-carboxylic acidYield 26.4%

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 6-bromo-pyridine-2-carboxylic acid (CAN 21190-87-4, 0.375 g, 1.86 mmol), 2-cyclopentenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (CAN 287944-10-9, 0.3 g, 1.6 mmol), Pd(dppf)Cl2 (CAN 95464-05-4, 0.06 g, 0.08 mmol) and K2CO3 (0.642 g, 4.7 mmol) in DMF (10 mL) and water (1 mL) was heated to 100° C. overnight. After filtration, the filtrate was concentrated and the residue was purified by column chromatography (silica gel, 15 g, eluting with 10% ethyl acetate in petroleum ether) to give the title compound (0.08 g, 23%) as white solid; MS (EI): m/e=190.1 [M+H]+.

Workup

  1. filtrationAfter filtration
  2. concentrationthe filtrate was concentrated
  3. customthe residue was purified by column chromatography (silica gel, 15 g, eluting with 10% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-cada55bfb0d947829096d471abdd01bc
Source dataset
uspto-grants-2016_04
Patent number
US09321727B2

Linked notes

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