Potassium Phosphate, Tribasic → Methyl 2-(benzo[d]thiazol-5-yl)-3-(isopropyl(methyl)amino)quinoxaline-6-carboxylate

HRID 1403411Notes

Reaction equation

[CH:1]([N:4]([CH3:27])[C:5]1[C:6](OS(C(F)(F)F)(=O)=O)=[N:7][C:8]2[C:13]([N:14]=1)=[CH:12][C:11]([C:15]([O:17][CH3:18])=[O:16])=[CH:10][CH:9]=2)([CH3:3])[CH3:2].CC1(C)C(C)(C)OB([C:36]2[CH:37]=[CH:38][C:39]3[S:43][CH:42]=[N:41][C:40]=3[CH:44]=2)O1.[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:43]1[C:39]2[CH:38]=[CH:37][C:36]([C:6]3[C:5]([N:4]([CH:1]([CH3:2])[CH3:3])[CH3:27])=[N:14][C:13]4[C:8](=[CH:9][CH:10]=[C:11]([C:15]([O:17][CH3:18])=[O:16])[CH:12]=4)[N:7]=3)=[CH:44][C:40]=2[N:41]=[CH:42]1

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of methyl 3-(isopropyl(methyl)amino)-2-(trifluoromethylsulfonyloxy)quinoxaline-6-carboxylate (150 mg, 0.37 mmol) in dioxane (5 mL) was added 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d]thiazole (288 mg, 1.1 mmol), K3PO4 (234 mg, 1.1 mmol), Pd(PPh3)4 (21 mg, 0.018 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 2%-5% ethyl acetate in petroleum ether to afford methyl 2-(benzo[d]thiazol-5-yl)-3-(isopropyl(methyl)amino)quinoxaline-6-carboxylate as a yellow solid (120 mg, 83%).

Workup

concentrationconcentrated in vacuo
customto give a residue, which
customwas purified by silica gel column chromatography
washeluting with 2%-5% ethyl acetate in petroleum ether

Sources & evidence

ORD record: ord-cb651d6596384eed84fabaa257f33c57
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08912188B2

Reaction notes

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