Iodine → 6-(5-Iodoisoxazol-3-yl)isoquinoline

HRID 598848Notes

Reaction equation

C([Sn](CCCC)(CCCC)[C:6]1[O:10][N:9]=[C:8]([C:11]2[CH:12]=[C:13]3[C:18](=[CH:19][CH:20]=2)[CH:17]=[N:16][CH:15]=[CH:14]3)[CH:7]=1)CCC.[I:29]I>C1COCC1>[I:29][C:6]1[O:10][N:9]=[C:8]([C:11]2[CH:12]=[C:13]3[C:18](=[CH:19][CH:20]=2)[CH:17]=[N:16][CH:15]=[CH:14]3)[CH:7]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 6-(5-(tributylstannyl)isoxazol-3-yl)isoquinoline (1.00 g, 2.1 mmol) in 20 mL of THF in a sealable tube was added iodine (0.52 g, 2.1 mmol). The tube was sealed and heated to 80° C. by immersion in an oil bath. After 12 hours, the mixture was concentrated under reduced pressure and the residue was purified by flash chromatography on silica gel (0 to 2.5% MeOH/DCM), affording 6-(5-iodoisoxazol-3-yl)isoquinoline (0.60 g, 90% yield) as a grey powder. 1H NMR (400 MHz, DMSO-d6) δ ppm 9.40 (s, 1H), 8.59 (d, J=5.6 Hz, 1H), 8.52 (s, 1H), 8.27 (d, J=8.6 Hz, 1H), 8.12 (dd, J=1.6 Hz, 8.6 Hz, 1H), 7.92 (d, J=5.7 Hz, 1H).

Workup

customThe tube was sealed
concentrationthe mixture was concentrated under reduced pressure
customthe residue was purified by flash chromatography on silica gel (0 to 2.5% MeOH/DCM)

Sources & evidence

ORD record: ord-2c748c0c391f4b848e598d31d9788a27
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07897619B2

Reaction notes

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