Toluene → Ethyl 3-(pyridin-2-yl)benzoate

HRID 383763Notes

Reaction equation

[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[C:8](B(O)O)[CH:9]=[CH:10][CH:11]=1)=[O:5])[CH3:2].Br[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=1.C(=O)([O-])[O-].[K+].[K+].C1(C)C=CC=CC=1>CCO.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>[N:17]1[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=1[C:8]1[CH:7]=[C:6]([CH:11]=[CH:10][CH:9]=1)[C:4]([O:3][CH2:1][CH3:2])=[O:5]

Participants

Conditions

Temperature: 100 °C

Procedure

Tetrakis(triphenylphosphine)palladium(0) (208 mg, 0.180 mmol) was added to a solution of 3-ethoxycarbonylphenyl boronic acid (350 mg, 1.80 mmol), 2 -bromopyridine (189 μL, 1.99 mmol) and potassium carbonate (499 mg, 3.61 mmol) in EtOH:toluene (4.00 mL of an 80:20 mixture, respectively) at rt. The resulting solution was heated to 100° C. in a sealed microwave vial for a total of 15 min. After cooling to rt, the reaction mixture was filtered through a short column of Celite®, eluting with EtOAc. The filtrate was washed with water and brine, dried (sodium sulfate) and concentrated in vacuo. The crude residue was purified by flash chromatography on silica gel (isocratic elution; 10% EtOAc/hexanes as eluent) to afford the title compound i-2a. m/z (ES) 228 (MH)+.

Workup

customat rt
temperatureAfter cooling to rt
filtrationthe reaction mixture was filtered through a short column of Celite®
washeluting with EtOAc
washThe filtrate was washed with water and brine
dry with materialdried (sodium sulfate)
concentrationconcentrated in vacuo
customThe crude residue was purified by flash chromatography on silica gel (isocratic elution; 10% EtOAc/hexanes as eluent)

Sources & evidence

ORD record: ord-ce435e7778c44aaaabbcde55e32d390c
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08367679B2

Reaction notes

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