2-(Tributylstannyl)-1,3-thiazole → HCID 10132406, compound

HRID 586331Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]([C:8]2[N:12]3[N:13]=[CH:14][C:15]([C:17]([F:20])([F:19])[F:18])=[N:16][C:11]3=[N:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1.C([Sn](CCCC)(CCCC)[C:26]1[S:27][CH:28]=[CH:29][N:30]=1)CCC>C1COCC1.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>[S:27]1[CH:28]=[CH:29][N:30]=[C:26]1[C:2]1[CH:3]=[C:4]([C:8]2[N:12]3[N:13]=[CH:14][C:15]([C:17]([F:20])([F:19])[F:18])=[N:16][C:11]3=[N:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 65 °C

Procedure

A mixture of 7-(3-bromophenyl)-3-trifluoromethylimidazo[1,2-b][1,2,4]triazine (0.2 g, 0.58 mmol), 2-tributylstannylthiazole (0.44 g, 1.17 mmol) and tetrakis(triphenylphosphine)palladium(0) (67 mg, 0.06 mmol) in THF (2 ml) was degassed with a stream of N2 for 10 min and stirred at 65° C. for 12 h. After allowing to cool to room temperature, the mixture was concentrated in vacuo. The residue was purified by flash chromatography (silica gel, 25% EtOAc/isohexane) and triturated with Et2O to give 64 mg (32%) of the title compound: 1H NMR (360 MHz, CDCl3) δ 7.42 (1H, d, J 3.2 Hz), 7.65 (1H, t, J 7.9 Hz), 7.94 (1H, d, J 3.2 Hz), 8.04 (1H, dq, J 7.9, 1.0 Hz), 8.06 (1H, dq, J 7.9, 1.0 Hz), 8.71 (1H, s), 8.76 (1H, t, J 1.6 Hz), 8.86 (1H, s); MS (ES+) m/z 348 [M+H]+.

Workup

customwas degassed with a stream of N2 for 10 min
temperatureto cool to room temperature
concentrationthe mixture was concentrated in vacuo
customThe residue was purified by flash chromatography (silica gel, 25% EtOAc/isohexane)
customtriturated with Et2O

Sources & evidence

ORD record: ord-840b9204a91844aca3ed0b40a2e8f301
Source dataset: uspto-grants-2005_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06936608B2

Reaction notes

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