Benzo(B)Thiophene-2-Boronic Acid → HCID 70664597, compound

HRID 1403404Notes

Reaction equation

[N:1]1([C:7]2[C:8](OS(C(F)(F)F)(=O)=O)=[N:9][C:10]3[C:15]([N:16]=2)=[CH:14][C:13]([C:17]([O:19][CH3:20])=[O:18])=[CH:12][CH:11]=3)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[S:29]1[C:33](B(O)O)=[CH:32][C:31]2[CH:37]=[CH:38][CH:39]=[CH:40][C:30]1=2.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.O.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:29]1[C:33]([C:8]2[C:7]([N:1]3[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]3)=[N:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([C:17]([O:19][CH3:20])=[O:18])[CH:14]=3)[N:9]=2)=[CH:32][C:31]2[CH:37]=[CH:38][CH:39]=[CH:40][C:30]1=2

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of methyl 3-(piperidin-1-yl)-2-(trifluoromethylsulfonyloxy)quinoxaline-6-carboxylate (280 mg, crude) in dioxane (5 mL) was added benzo[b]thiophen-2-ylboronic acid (357 mg, 2.0 mmol), K3PO4 (425 mg, 2.0 mmol), Pd(PPh3)4 (39 mg, 0.033 mmol) and water (3 drops). The resulting solution was stirred for 1 h at 90° C. and then concentrated in vacuo to give a residue, which was purified by silica gel column chromatography eluting with 3.3% ethyl acetate in petroleum ether to afford methyl 2-(benzo[b]thiophen-2-yl)-3-(piperidin-1-yl)quinoxaline-6-carboxylate as a yellow solid (100.0 mg, 37% 2 steps).

Workup

concentrationconcentrated in vacuo
customto give a residue, which
customwas purified by silica gel column chromatography
washeluting with 3.3% ethyl acetate in petroleum ether

Sources & evidence

ORD record: ord-ed959fd8658749e88fa2bfd16262de26
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08912188B2

Reaction notes

Loading…