3-(Tributylstannyl)pyridine → HCID 69895842, compound

HRID 1794295Notes

Reaction equation

Br[C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][N:7]3[C:13]([C:14]4[C:15]([C:20]5[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=5)=[N:16][O:17][C:18]=4[CH3:19])=[N:12][N:11]=[C:8]32)=[CH:4][CH:3]=1.C([Sn](CCCC)(CCCC)[C:31]1[CH:32]=[N:33][CH:34]=[CH:35][CH:36]=1)CCC>CN(C=O)C>[CH3:19][C:18]1[O:17][N:16]=[C:15]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:14]=1[C:13]1[N:7]2[CH2:6][C:5]3[C:9]([C:8]2=[N:11][N:12]=1)=[CH:10][C:2]([C:31]1[CH:32]=[N:33][CH:34]=[CH:35][CH:36]=1)=[CH:3][CH:4]=3

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 8-bromo-3-(5-methyl-3-phenylisoxazol-4-yl)-5H-[1,2,4]triazolo[3,4-a]isoindole (100 mg) (as prepared in Example 4), 3-(tri-n-butylstannyl)pyridine (442 mg) and DMF (5 ml) was degassed with a stream of N2 for 0.5 h. Bis(triphenylphosphine)palladium(II) chloride (5 mg) was added and the reaction heated to 100° C. for 2 h. The mixture was concentrated under reduced pressure and the residue purified by column chromatography on silica, eluting with 2.5% MeOH/CH2Cl2 to give the title compound (75 mg, 64%). 1H NMR (400 MHz, CDCl3) δ 8.66 (1H, t, J=3.3 Hz), 8.23 (1H, d, J=1.4 Hz), 7.95–7.92 (1H, m), 7.63 (1H, dd, J=8.0, 1.7 Hz), 7.57–7.54 (2H, m), 7.49–7.38 (5H, m), 4.07 (2H, s), 3.97 (2H, s), 2.73 (3H, s), m/z (ES+) 392 (M+H)+.

Workup

customwas degassed with a stream of N2 for 0.5 h
additionBis(triphenylphosphine)palladium(II) chloride (5 mg) was added
concentrationThe mixture was concentrated under reduced pressure
customthe residue purified by column chromatography on silica
washeluting with 2.5% MeOH/CH2Cl2

Sources & evidence

ORD record: ord-eb4c6ede03fa4052957e5fd0bc468fbb
Source dataset: uspto-grants-2006_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07022724B2

Reaction notes

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