3-(Tributylstannyl)pyridine → 6-pyridin-3-yl-2-(2-quinolin-2-ylethyl)[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one

HRID 1777787Notes

Reaction equation

Br[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8](=[O:23])[N:9]([CH2:11][CH2:12][C:13]3[CH:22]=[CH:21][C:20]4[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=4)[N:14]=3)[N:10]=2)[CH:7]=1.C([Sn](CCCC)(CCCC)[C:29]1[CH:30]=[N:31][CH:32]=[CH:33][CH:34]=1)CCC>CN(C=O)C.CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C>[N:31]1[CH:32]=[CH:33][CH:34]=[C:29]([C:2]2[CH:3]=[CH:4][C:5]3[N:6]([C:8](=[O:23])[N:9]([CH2:11][CH2:12][C:13]4[CH:22]=[CH:21][C:20]5[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=5)[N:14]=4)[N:10]=3)[CH:7]=2)[CH:30]=1

Participants

Conditions

Temperature: 135 °C

Procedure

In a 2 mL microwave vial were placed 3-4 (15 mg, 0.041 mmol), 3-(tributylstannyl)pyridine (16 mg, 0.045 mmol), and bis(tri-tert-butylphosphine)palladium (2 mg, 0.004 mmol) in anhydrous DMF (0.4 mL). The vial was sealed and the reaction was heated at 135° C. under microwave irradiation for 15 min. The reaction mixture was filtered, and the filtrate was directly purified by reversed phase HPLC to give 5.0 mg (35%) of 9-1. 1H NMR (500 MHz, DMSO-d6): δ 9.03 (s, 1H), 8.67 (d, J=5.0 Hz, 1H), 8.51 (d, J=8.4 Hz, 1H), 8.34 (d, J=8.0 Hz, 1H), 8.29 (s, 1H), 8.04 (d, J=8.1 Hz, 1H), 7.98 (d, J=8.5 Hz, 1H), 7.83 (t, J=7.6 Hz, 1H), 7.69-7.61 (m, 4H), 7.38 (d, J=9.8 Hz, 1H), 4.47 (t, J=6.9 Hz, 2H), 2.54 (t, J=6.9 Hz, 2H). HRMS (ES) 368.1502 (M+H) found, 368.1509 required.

Workup

customThe vial was sealed
filtrationThe reaction mixture was filtered
customthe filtrate was directly purified by reversed phase HPLC

Sources & evidence

ORD record: ord-a7b16b91d52d4d7eb6582fbbc43072aa
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09266881B2

Reaction notes

Loading…