Hydrochloric Acid → 1-(2,3-Dihydro-[1,4]dioxino[2,3-b]pyridin-7-yl)ethan-1-one

HRID 1038584Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]2[O:11][CH2:10][CH2:9][O:8][C:5]2=[N:6][CH:7]=1.[CH2:12]([O:14]C([Sn](CCCC)(CCCC)CCCC)=C)[CH3:13].Cl>C1(C)C=CC=CC=1.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:11]1[C:4]2[C:5](=[N:6][CH:7]=[C:2]([C:12](=[O:14])[CH3:13])[CH:3]=2)[O:8][CH2:9][CH2:10]1

Participants

Conditions

Temperature: 100 °C

Procedure

Under an argon atmosphere, 7-bromo-2,3-dihydro-[1,4]dioxino[2,3-b]pyridine (65 mg, 0.30 mmol) was dissolved in toluene (1.5 mL), added tetrakis(triphenylphosphine)palladium (35 mg, 0.03 mmol) and 1-ethoxyethenyl tri n-butyl tin (112 ΞL, 0.33 mmol), and the mixture was stirred at 100° C. overnight. The reaction solution was reverted to room temperature, and added 1N hydrochloric acid. The reaction solution was filtered through a pad of celite. The reaction solution was added ethyl acetate for extraction. The organic layer was washed with brine, dried over anhydrous sodium sulfate, concentrated in vacuo, and purified by preparative thin-layer chromatography (n-hexane/ethyl acetate=1/1). The title compound (37 mg (yield 69%)) was obtained as a white solid.

Workup

customwas reverted to room temperature
filtrationThe reaction solution was filtered through a pad of celite
additionThe reaction solution was added ethyl acetate
extractionfor extraction
washThe organic layer was washed with brine
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated in vacuo
custompurified by preparative thin-layer chromatography (n-hexane/ethyl acetate=1/1)

Sources & evidence

ORD record: ord-4bf9fc92f3c143c6a96324bd6b516291
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08551985B2

Reaction notes

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