1,2-Dimethoxyethane → 6-(3-Chloro-phenyl)-pyridine-2-carboxylic acid methyl ester

HRID 33536

Reaction equation

HRID 33536 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4](B2OC(C)(C)C(C)(C)O2)[CH:5]=[CH:6][CH:7]=1.[C:17](=[O:20])([O-])[O-:18].[Cs+].[Cs+].COC([C:27]1[CH:28]=[N:29][CH:30]=[C:31](Br)[CH:32]=1)=O.[CH2:34](COC)OC>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:34][O:18][C:17]([C:28]1[CH:27]=[CH:32][CH:31]=[C:30]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=2)[N:29]=1)=[O:20]

Participants

6

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 10796Cesium carbonateHCID 699336Methyl 5-bromopyridine-3-carboxylateHCID 100372252-(3-Chlorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Product 1

HCID 691068496-(3-Chloro-phenyl)-pyridine-2-carboxylic acid methyl esterYield 83%

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Procedure

104 mg (0.09 mmol)Pd(PPh3)4, 1.5 g (6.29 mmol) of 3-chlorophenylboronic acid pinacol ester 2.86 ml (8.58 mmol) and 3M cesium carbonate solution were added under argon at room temperature to a solution of 1.24 g (5.72 mmol) methyl-5-bromo-pyridine-3-carboxylate in 45 ml dimethoxyethane and the mixture was heated to reflux for 30 min. The reaction mixture was cooled to room temperature and evaporated. The residue was taken up with ethyl acetate, washed with water, dried over sodium sulphate and evaporated. Chromatography on silica (eluent: ethyl acetate/n-heptane 1:3) gave 1.42 g (83%) of 6-(3-Chloro-phenyl)-pyridine-2-carboxylic acid methyl ester

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 30 min
  3. customevaporated
  4. washwashed with water
  5. dry with materialdried over sodium sulphate
  6. customevaporated

Sources & evidence

ORD record
ord-0a866843f27743d892c6a85afdab0db5
Source dataset
uspto-grants-2008_09
Patent number
US07429605B2

Linked notes

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