Sodium Carbonate → 5-Bromo-2-(4-methoxyphenyl)pyridin-3-amine

HRID 1431556Notes

Reaction equation

Br[C:2]1[C:7]([NH2:8])=[CH:6][C:5]([Br:9])=[CH:4][N:3]=1.[CH3:10][O:11][C:12]1[CH:17]=[CH:16][C:15](B(O)O)=[CH:14][CH:13]=1.C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1.O.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>[Br:9][C:5]1[CH:6]=[C:7]([NH2:8])[C:2]([C:15]2[CH:16]=[CH:17][C:12]([O:11][CH3:10])=[CH:13][CH:14]=2)=[N:3][CH:4]=1

Participants

Conditions

Temperature: 90 °C

Procedure

A stirred mixture of 2,5-dibromopyridin-3-amine (860 mg, 3.41 mmol), 4-methoxyphenylboronic acid (519 mg, 3.41 mmol), trans-dichlorobis(triphenylphosphine)palladium (II) (120.5 mg, 0.17 mmol), and 2.0M sodium carbonate (5.1 mL, 10.2 mmol) in 1,4-dioxane (15 mL) was heated to 90° C. After 19 h, the reaction was cooled to rt then diluted with water. After extraction with EtOAc, the organic extraction was dried over anhydrous sodium sulfate. After filtration and concentration, the residue was purified on silica gel (0-20% EtOAc in hexanes) to afford a white solid as 5-bromo-2-(4-methoxyphenyl)pyridin-3-amine. 1H NMR (400 MHz, CDCl3) δ ppm 8.15 (1H, d, J=2.0 Hz), 7.65 (2H, m), 7.20 (1H, d, J=2.0 Hz), 7.06 (2H, m), 4.11 (5H, m).

Workup

temperaturethe reaction was cooled to rt
extractionAfter extraction with EtOAc
extractionthe organic extraction
dry with materialwas dried over anhydrous sodium sulfate
filtrationAfter filtration and concentration
customthe residue was purified on silica gel (0-20% EtOAc in hexanes)

Sources & evidence

ORD record: ord-100c871867824bbfb9a16e3d09eb9515
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08940724B2

Reaction notes

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