Benzo(B)Thiophene-2-Boronic Acid → Methyl 3-(azepan-1-yl)-2-(benzo[b]thiophen-2-yl)quinoxaline-6-carboxylate

HRID 1403407Notes

Reaction equation

HRID 1403407 reaction equation
[N:1]1([C:8]2[C:9](OS(C(F)(F)F)(=O)=O)=[N:10][C:11]3[C:16]([N:17]=2)=[CH:15][C:14]([C:18]([O:20][CH3:21])=[O:19])=[CH:13][CH:12]=3)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[S:30]1[C:34](B(O)O)=[CH:33][C:32]2[CH:38]=[CH:39][CH:40]=[CH:41][C:31]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>[N:1]1([C:8]2[C:9]([C:34]3[S:30][C:31]4[CH:41]=[CH:40][CH:39]=[CH:38][C:32]=4[CH:33]=3)=[N:10][C:11]3[C:16]([N:17]=2)=[CH:15][C:14]([C:18]([O:20][CH3:21])=[O:19])=[CH:13][CH:12]=3)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

7

Reactant 3

HCID 2359Benzo(B)Thiophene-2-Boronic AcidHCID 62657Potassium Phosphate, TribasicHCID 86670563Methyl 3-(azepan-1-yl)-2-(trifluoromethylsulfonyloxy)quinoxaline-6-carboxylate

Product 1

HCID 70664777Methyl 3-(azepan-1-yl)-2-(benzo[b]thiophen-2-yl)quinoxaline-6-carboxylateYield 34%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of methyl 3-(azepan-1-yl)-2-(trifluoromethylsulfonyloxy)quinoxaline-6-carboxylate (250 mg, crude) in dioxane (2 mL) was added benzo[b]thiophen-2-ylboronic acid (180 mg, 1.00 mmol), K3PO4 (210 mg, 1.00 mmol) and Pd(PPh3)4 (29 mg, 0.025 mmol) under nitrogen atmosphere. After stirring 1 h at 90° C., the reaction mixture was dissolved in water (25 mL), extracted with dichloromethane (3×30 mL), dried over anhydrous magnesium sulfate and concentrated under reduced pressure to afford a residue, which was purified by silica gel column chromatography eluting with 2% ethyl acetate in petroleum ether to afford methyl 3-(azepan-1-yl)-2-(benzo[b]thiophen-2-yl)quinoxaline-6-carboxylate as a light yellow solid (82 mg).

Workup

  1. extractionextracted with dichloromethane (3×30 mL)
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customto afford a residue, which
  5. customwas purified by silica gel column chromatography
  6. washeluting with 2% ethyl acetate in petroleum ether

Sources & evidence

ORD record
ord-8dd197f91e5743ffba32bdbb3034ddf5
Source dataset
uspto-grants-2014_12
Patent number
US08912188B2

Reaction notes

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