Diethyl Ether → 3-(2-Bromophenyl)-5-chloro-2-(benzyloxy)pyridine

HRID 269582Notes

Reaction equation

[CH2:1]([O:8][C:9]1[C:14](Br)=[CH:13][C:12]([Cl:16])=[CH:11][N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1B(O)O.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>[Br:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[C:14]1[C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[N:10][CH:11]=[C:12]([Cl:16])[CH:13]=1

Participants

Conditions

Temperature: 70 °C

Procedure

2-(Benzyloxy)-3-bromo-5-chloropyridine (150 mg, 0.5 mmol) and 2-bromophenylboronic acid (100 mg, 0.5 mmol) were dissolved in toluene/ethanol (1:1, 5 ml) under nitrogen. Potassium carbonate (550 mg, 4 mmol) was added, followed by tetrakis(triphenylphosphine)palladium(0) (58 mg, 0.05 mmol). The resulting mixture was heated at 70° C. in a Smithcreator® microwave for 10 minutes. After cooling, diethyl ether(10 ml) and water (10 ml) were added, The organic layer was washed with water, dried (MgSO4) and evaporated. The product was purified by flash chromatography (silica gel, 2% ethyl acetate:isohexane) to give the title compound as a clear oil (80 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% ethyl acetate:isohexane)

Sources & evidence

ORD record: ord-0619a99b59864bf8a00077c1d42ed192
Source dataset: uspto-grants-2008_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07446222B2

Reaction notes

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