Ethyl Acetate → 3-Bromo-2-(4-fluorophenyl)pyridine

HRID 1773674Notes

Reaction equation

Br[C:2]1[C:7]([Br:8])=[CH:6][CH:5]=[CH:4][N:3]=1.[F:9][C:10]1[CH:15]=[CH:14][C:13](B(O)O)=[CH:12][CH:11]=1.C([O-])([O-])=O.[Na+].[Na+].CCOC(C)=O>O1CCOCC1.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:8][C:7]1[C:2]([C:13]2[CH:14]=[CH:15][C:10]([F:9])=[CH:11][CH:12]=2)=[N:3][CH:4]=[CH:5][CH:6]=1

Participants

Conditions

Temperature: 80 °C

Procedure

In a 2-5 mL Smith Process Vial, 2,3-dibromopyridine (300.0 mg, 1.266 mmol), 4-fluorophenyl boronic acid (177.2 mg, 1.266 mmol, 1 equiv) and Pd(PPh3)4 (73.2 mg, 0.063 mmol, 0.05 equiv) were placed. The mixture was suspended in 1,4-dioxane (3 mL) and 2M-Na2CO3 (1 mL) under a nitrogen atmosphere. The mixture was heated at 80° C. for 10 min using the microwave reactor. To the mixture were added EtOAc (70 mL) and water (30 mL). The whole was filtered through Celite (3 g) and the filtrate was washed with brine (30 mL), dried over Na2SO4 and concentrated under a reduced pressure. Obtained crude material was purified by Gilson preparative HPLC to give 3-bromo-2-(4-fluorophenyl)pyridine.

Workup

filtrationThe whole was filtered through Celite (3 g)
washthe filtrate was washed with brine (30 mL)
dry with materialdried over Na2SO4
concentrationconcentrated under a reduced pressure
customObtained crude material
customwas purified by Gilson preparative HPLC

Sources & evidence

ORD record: ord-247e22918640473f88a7e70a954d8f7e
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09255089B2

Reaction notes

Loading…