Tetramethyltin → Ethyl 7-hydroxy-4-methyl-3-phenylisoxazolo[4,5-c]pyridine-6-carboxylate

HRID 2388208Notes

Reaction equation

Br[C:2]1[C:7]2[C:8]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[N:9][O:10][C:6]=2[C:5]([OH:17])=[C:4]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[N:3]=1.[CH3:23][Sn](C)(C)C>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.CN(C=O)C>[OH:17][C:5]1[C:6]2[O:10][N:9]=[C:8]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:7]=2[C:2]([CH3:23])=[N:3][C:4]=1[C:18]([O:20][CH2:21][CH3:22])=[O:19]

Participants

Conditions

Temperature: 125 °C

Procedure

A nitrogen flushed flask was charged with ethyl 4-bromo-7-hydroxy-3-phenylisoxazolo[4,5-c]pyridine-6-carboxylate (150 mg, 0.413 mmol), DMF (2 mL), tetramethylstannane (0.17 mL, 1.24 mmol), and Pd(PPh3)2Cl2 (58 mg, 0.083 mmol). The mixture was heated in an oil bath (bath temperature=120-130° C.) for 2 hours. After the reaction mixture was cooled to room temperature, it was purified by flash chromatography (0-30% EtOAc/hexanes) to afford 41 mg of the title compound. MS: (+) m/z 299.43 (M+1).

Workup

temperatureAfter the reaction mixture was cooled to room temperature
customit was purified by flash chromatography (0-30% EtOAc/hexanes)

Sources & evidence

ORD record: ord-5ca68454959844b29987d66283d541df
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08269008B2

Reaction notes

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