3-(Tributylstannyl)pyridine → HCID 136335914, compound

HRID 1847222Notes

Reaction equation

[CH2:1]([O:3][C:4]([C:6]1[C:7]([OH:22])=[C:8]2[C:15]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[N:14][S:13][C:9]2=[C:10](Br)[N:11]=1)=[O:5])[CH3:2].C([Sn](CCCC)(CCCC)[C:28]1[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=1)CCC>CN(C=O)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>[CH2:1]([O:3][C:4]([C:6]1[C:7]([OH:22])=[C:8]2[C:15]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[N:14][S:13][C:9]2=[C:10]([C:28]2[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=2)[N:11]=1)=[O:5])[CH3:2]

Participants

Conditions

Temperature: 120 °C

Procedure

To a solution of 7-bromo-4-hydroxy-3-phenyl-isothiazolo[5,4-c]pyridine-5-carboxylic acid ethyl ester (180 mg, 0.47 mmol) in DMF (2.37 mL) was added 3-(tributylstannyl)pyridine (349 mg, 0.95 mmol) and PdCl2(PPh3)2 (33.3 mg, 0.047 mmol). The reaction mixture was stirred at 120° C. for 30 min. After cooling to r. t. the mixture was partitioned between water (150 mL) and EtOAc (150 mL). The organic layer was washed with brine, water, dried over MgSO4, and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel. Elution with 0-20% EtOAc/CH2Cl2 gave the title compound as white solid (28 mg): MS (m/z) 378.1 (M+1).

Workup

temperatureAfter cooling to r
customthe mixture was partitioned between water (150 mL) and EtOAc (150 mL)
washThe organic layer was washed with brine, water
dry with materialdried over MgSO4
concentrationconcentrated in vacuo
customThe residue was purified by flash column chromatography on silica gel
washElution with 0-20% EtOAc/CH2Cl2

Sources & evidence

ORD record: ord-559397b385544477829ecb55a7c10b8f
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08952160B2

Reaction notes

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