1,4-Dioxane → HCID 68193977, compound

HRID 1520146Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]([C:12]1[C:13](OS(C(F)(F)F)(=O)=O)=[N:14][C:15]3[C:20]([N:21]=1)=[CH:19][C:18]([C:22]([O:24][CH3:25])=[O:23])=[CH:17][CH:16]=3)[CH2:7][CH2:6][CH2:5]2.[F:34][C:35]1[CH:36]=[CH:37][C:38]2O[C:41](B(O)O)=[CH:40][C:39]=2[CH:46]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].O1CCOC[CH2:56]1>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>[F:34][C:35]1[CH:46]=[C:39]2[C:38](=[CH:37][CH:36]=1)[CH2:56][C:41]([C:13]1[C:12]([N:8]3[C:9]4[C:4](=[CH:3][C:2]([F:1])=[CH:11][CH:10]=4)[CH2:5][CH2:6][CH2:7]3)=[N:21][C:20]3[C:15](=[CH:16][CH:17]=[C:18]([C:22]([O:24][CH3:25])=[O:23])[CH:19]=3)[N:14]=1)=[CH:40]2

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of methyl 3-(6-fluoro-3,4-dihydroquinolin-1(2H)-yl)-2-(trifluoromethylsulfonyloxy)quinoxaline-6-carboxylate (From Ex. 6, step 3, 200 mg, crude) in dioxane (5.0 mL) and three drops of water was added 5-fluorobenzofuran-2-ylboronic acid (210 mg, 1.07 mmol), K3PO4 (272 mg, 1.29 mmol) and Pd(PPh3)4 (25 mg, 0.02 mmol). The reaction was stirred for 1 h at 90° C. under an inert atmosphere of nitrogen in an oil bath. The reaction mixture was concentrated under vacuum to give the residue, which was purified by a silica gel column with 1% to 5% ethyl acetate in petroleum to afford methyl 2-(5-fluoro-1H-inden-2-yl)-3-(6-fluoro-3,4-dihydroquinolin-1(2H)-yl)quinoxaline-6-carboxylate as a light red solid (59 mg).

Workup

concentrationThe reaction mixture was concentrated under vacuum
customto give the residue, which
customwas purified by a silica gel column with 1% to 5% ethyl acetate in petroleum

Sources & evidence

ORD record: ord-6252845f2c4f457ab2acf452e21ac0d4
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09073902B2

Reaction notes

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