2-(Tributylstannyl)pyridine → HCID 66633234, compound

HRID 409018Notes

Reaction equation

Cl[C:2]1[N:7]=[C:6]2[S:8][CH:9]=[CH:10][C:5]2=[CH:4][C:3]=1[CH:11]([N:13]1[C:21](=[O:22])[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:14]1=[O:23])[CH3:12].C([Sn](CCCC)(CCCC)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][N:30]=1)CCC>O1CCOCC1.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>[N:30]1[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=1[C:2]1[N:7]=[C:6]2[S:8][CH:9]=[CH:10][C:5]2=[CH:4][C:3]=1[CH:11]([N:13]1[C:21](=[O:22])[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:14]1=[O:23])[CH3:12]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 2-(1-(6-chlorothieno[2,3-b]pyridin-5-yl)ethyl)isoindoline-1,3-dione (300 mg, 0.875 mmol), 2-(tributylstannyl)pyridine (340 μL, 1.05 mmol, 1.2 eq) and tetrakis(triphenylphosphine)palladium(0) (101 mg, 0.0875 mmol, 0.1 eq) was dissolved in 10 mL of dioxane under nitrogen. The reaction was heated to 100° C. for 2 days, cooled to rt and concentrated in vacuo. Purification by column chromatography using ethyl acetate/hexanes afforded 2-(1-(6-(pyridin-2-yl)-thieno[2,3-b]pyridin-5-yl)ethyl)isoindoline-1,3-dione. LC/MS (M+1, found=386.0). 1H NMR (400 MHz, CDCl3) δ 8.69 (s, 1H), 8.66 (ddd, J=4.9, 1.6, 0.8 Hz, 1H), 7.76 (td, J=7.8, 1.8 Hz, 1H), 7.73-7.62, series of m, 5H), 7.57 (d, J=5.9 Hz, 1H), 7.36 (d, J=5.9 Hz, 1H), 7.31 (ddd, J=7.2, 4.7, 1.4 Hz, 1H), 6.33 (q, J=7.2 Hz, 1H), 1.99 (d, J=7.2 Hz, 3H) ppm.

Workup

temperaturecooled to rt
concentrationconcentrated in vacuo
customPurification by column chromatography

Sources & evidence

ORD record: ord-b4ed893ca04a406981cb28cadc758714
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08759371B2

Reaction notes

Loading…