3-(Tributylstannyl)pyridine → HCID 9998304, compound

HRID 891864Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]([C:9]2[N:13]3[N:14]=[CH:15][C:16]([C:18]([F:21])([F:20])[F:19])=[N:17][C:12]3=[N:11][CH:10]=2)[CH:5]=[CH:6][C:7]=1[CH3:8].C([Sn](CCCC)(CCCC)[C:27]1[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=1)CCC>O1CCCC1.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>[CH3:8][C:7]1[CH:6]=[CH:5][C:4]([C:9]2[N:13]3[N:14]=[CH:15][C:16]([C:18]([F:21])([F:20])[F:19])=[N:17][C:12]3=[N:11][CH:10]=2)=[CH:3][C:2]=1[C:27]1[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=1

Participants

Conditions

Temperature: 80 °C

Procedure

7-(3-Bromo-4-methylphenyl)-3-trifluoromethylimidazo[1,2-b][1,2,4]triazine (28 mg, 78 μmol) was dissolved in tetrahydrofuran (3 ml) under nitrogen and degassed for 10 min before 3-(tributylstannyl)pyridine (37 mg, 100 μmol) and tetrakis(triphenylphosphine)palladium(0) (10 mg, 9 μmol) were added. The stirred mixture was heated at 80° C. for 48 h. Solvent was removed in vacuo and the residue purified by chromatography (silica gel, 50% EtOAc/isohexane) to give 12 mg of the title compound as a yellow solid: 1H NMR (400 MHz, CDCl3) δ 2.37 (3H, s), 7.40–7.44 (1H, m), 7.50 (1H, d, J 8.2), 7.71–7.75 (1H, m), 7.98 (1H, d, J 1.9), 8.03 (1H, dd, J 1.9, 8.0), 8.62 (1H, s), 8.65–8.68 (2H, m), 8.79 (1H, s); MS (ES+) m/z 356 [M+H]+.

Workup

additionwere added
customSolvent was removed in vacuo
customthe residue purified by chromatography (silica gel, 50% EtOAc/isohexane)

Sources & evidence

ORD record: ord-67b7f9e1f9bb43c596616b2c811607fc
Source dataset: uspto-grants-2006_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07005431B2

Reaction notes

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