Cesium carbonate → Methyl 5-(4-chlorophenyl)nicotinate

HRID 33532

Reaction equation

HRID 33532 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[N:7][CH:8]=[C:9](Br)[CH:10]=1)=[O:4].C(=O)([O-])[O-].[Cs+].[Cs+].[Cl:18][C:19]1[CH:24]=[CH:23][C:22](B(O)O)=[CH:21][CH:20]=1>CN(C)C=O.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>[CH3:1][O:2][C:3](=[O:4])[C:5]1[CH:10]=[C:9]([C:22]2[CH:23]=[CH:24][C:19]([Cl:18])=[CH:20][CH:21]=2)[CH:8]=[N:7][CH:6]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 742994-Chlorophenylboronic acidHCID 699336Methyl 5-bromopyridine-3-carboxylate

Product 1

HCID 20099851Methyl 5-(4-chlorophenyl)nicotinateYield 79.4%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

81 mg (0.07 mmol)Pd(PPh3)4 was added under argon at room temperature to a solution of 1.0 g (4.63 mmol) methyl-5-bromo-pyridine-3-carboxylate in 23 ml N,N-dimethylformamide and the mixture was heated to 80° C. Then 2.26 g (6.94 mmol) cesium carbonate and 0.84 g (5.09 mmol) of 4-chlorophenyl boronic acid were added and the mixture was stirred at 80° C. over night. The reaction mixture was cooled to room temperature, filtered, and the filtrate evaporated. The residue was taken up with ethyl acetate, washed twice with water, dried over sodium sulphate and evaporated. Chromatography on silica (eluent: ethyl acetate/n-heptane 1:3) gave 0.91 g (69%) of 5-(4-Chloro-phenyl)-nicotinic acid methyl ester

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationfiltered
  3. customthe filtrate evaporated
  4. washwashed twice with water
  5. dry with materialdried over sodium sulphate
  6. customevaporated

Sources & evidence

ORD record
ord-d21b1b9b18a44c7d998890a5a019e51c
Source dataset
uspto-grants-2008_09
Patent number
US07429605B2

Linked notes

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