Diethyl Ether → 2'-{5-Chloro-2-(benzyloxy)-3-pyridinyl]-3-biphenylcarboxylic acid ethyl ester

HRID 269583Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:9]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[N:10][CH:11]=[C:12]([Cl:14])[CH:13]=1.[C:23]([C:28]1[CH:29]=[C:30](B(O)O)[CH:31]=[CH:32][CH:33]=1)([O:25][CH2:26][CH3:27])=[O:24].C(=O)([O-])[O-].[K+].[K+].C(OCC)C>C1(C)C=CC=CC=1.C(O)C.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.O>[CH2:26]([O:25][C:23]([C:28]1[CH:33]=[C:32]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[C:8]2[C:9]([O:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[N:10][CH:11]=[C:12]([Cl:14])[CH:13]=2)[CH:31]=[CH:30][CH:29]=1)=[O:24])[CH3:27]

Participants

Conditions

Temperature: 70 °C

Procedure

3-(2-Bromophenyl)-5-chloro-2-(benzyloxy)pyridine (80 mg, 0.214 mmol) and 3-(carbethoxy)phenylboronic acid (42 mg, 0.214 mmol) were dissolved in toluene/ethanol (1:1 1 ml) under nitrogen. Potassium carbonate (236 mg, 1.71 mmol) and tetrakis(triphenylphosphine)palladium(0) (25 mg, 0.0214 mmol) were added and the resulting mixture was heated at 70° C. in a Smithoreator® microwave for 15 minutes. After cooling, diethyl ether (5 ml) and water (5 ml) were added. The organic layer was washed with water, dried (MgSO4) and evaporated. The product was purified by flash chromatography (silica gel, 2-3% ethyl acetate:isohexane) to give the title compound as a clear oil (31 mg).

Workup

temperatureAfter cooling
washThe organic layer was washed with water
dry with materialdried (MgSO4)
customevaporated
customThe product was purified by flash chromatography (silica gel, 2-3% ethyl acetate:isohexane)

Sources & evidence

ORD record: ord-94873ed2ea5842daa7af2b7cde0255bc
Source dataset: uspto-grants-2008_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07446222B2

Reaction notes

Loading…