Sodium Carbonate → HCID 59631376, compound

HRID 1431446Notes

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.CC1(C)C(C)(C)OB([C:20]2[CH2:21][CH2:22][O:23][CH2:24][CH:25]=2)O1.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:20]2[CH2:25][CH2:24][O:23][CH2:22][CH:21]=2)=[N:3][CH:4]=1

Participants

Conditions

Temperature: 70 °C

Procedure

A stirred mixture of 2,5-dibromo-3-nitropyridine (0.31 g, 1.11 mmol), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,6-dihydro-2H-pyran (0.26 g, 1.23 mmol), tetrakis(triphenylphosphine)palladium (64.7 mg, 0.056 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 (0-20% EtOAc in hexanes) to afford a light yellow solid as 5-bromo-2-(3,6-dihydro-2H-pyran-4-yl)-3-nitropyridine. 1H NMR (400 MHz, CDCl3) δ ppm 8.81 (1H, d, J=2.0 Hz), 8.20 (1H, d, J=2.0 Hz), 6.09 (1H, m), 4.30 (2H, q, J=2.8 Hz), 3.94 (2H, t, J=5.4 Hz), 2.61 (2H, m).

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 (0-20% EtOAc in hexanes)

Sources & evidence

ORD record: ord-72f4baf9db16421e9e59e6f9e3925c22
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08940724B2

Reaction notes

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