Sodium Carbonate → HCID 59631229, compound

HRID 1431441Notes

Reaction equation

Br[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][C:5]([Br:11])=[CH:4][N:3]=1.[CH3:12][O:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1B(O)O.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.CCO.O.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>[Br:11][C:5]1[CH:6]=[C:7]([N+:8]([O-:10])=[O:9])[C:2]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[O:13][CH3:12])=[N:3][CH:4]=1

Participants

Conditions

Temperature: 70 °C

Procedure

A stirred mixture of 2,5-dibromo-3-nitropyridine (0.32 g, 1.13 mmol), 2-methoxybenzeneboronic acid (0.19 g, 1.25 mmol), tetrakis(triphenylphosphine)palladium (65.5 mg, 0.057 mmol), and 2.0M sodium carbonate (3.0 mL, 6.00 mmol) in toluene (3.0 mL) and EtOH (1.0 mL) was heated to 70° C. After 19 h, the reaction was cooled to rt then diluted with water. After extraction with EtOAc, the organic layer was dried over anhydrous sodium sulfate. After filtration and concentration, the residue was purified on silica gel (0-25% EtOAc in hexanes) to afford a light yellow solid as 5-bromo-2-(2-methoxyphenyl)-3-nitropyridine. 1H NMR (400 MHz, CDCl3) δ ppm 8.93 (1H, d, J=2.0 Hz), 8.37 (1H, d, J=2.0 Hz), 7.66 (1H, dd, J=7.5, 1.7 Hz), 7.52 (1H, m), 7.16 (1H, td, J=7.5, 1.0 Hz), 6.92 (1H, dd, J=8.3, 0.7 Hz), 3.72 (3H, s).

Workup

temperaturethe reaction was cooled to rt
extractionAfter extraction with EtOAc
dry with materialthe organic layer was dried over anhydrous sodium sulfate
filtrationAfter filtration and concentration
customthe residue was purified on silica gel (0-25% EtOAc in hexanes)

Sources & evidence

ORD record: ord-a1c33304d11a4d6e86455103d9a81b80
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08940724B2

Reaction notes

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