1,4-Dioxane → 3-Phenylpyridin-2-amine

HRID 1502586Notes

Reaction equation

[NH2:1][C:2]1[C:7](Br)=[CH:6][CH:5]=[CH:4][N:3]=1.[C:9]1(B(O)O)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(=O)(O)[O-].[Na+].O1CCOCC1>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O>[NH2:1][C:2]1[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

Conditions

Temperature: 150 °C

Procedure

A microwave vial was charged with 2-amino-3-bromopyridine (0.5 g, 2.9 mmol), phenylboronic acid (0.52 g, 4.3 mmol), sodium bicarbonate (0.31 g, 2.9 mmol), dichlorobis(triphenylphosphine)palladium(II) (0.1 g, 0.14 mmol), dioxane (5 mL) and water (1 mL). The vial was capped, and the reaction mixture was heated at 150° C. for 10 min. The reaction mixture was then cooled, quenched with water (10 mL), and extracted twice with ethyl acetate. The combined organic phases were dried (MgSO4) and concentrated to leave a black oil. The crude product was purified by chromatography on silica gel using 10-40% ethyl acetate/hexanes as eluant to provide the title compound as a white solid (0.35 g).

Workup

customThe vial was capped
temperatureThe reaction mixture was then cooled
customquenched with water (10 mL)
extractionextracted twice with ethyl acetate
dry with materialThe combined organic phases were dried (MgSO4)
concentrationconcentrated
customto leave a black oil
customThe crude product was purified by chromatography on silica gel using 10-40% ethyl acetate/hexanes as eluant

Sources & evidence

ORD record: ord-bb609cdc1560447bbdfead18dcd8ca96
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09210932B2

Reaction notes

Loading…