Water → HCID 70664762, compound

HRID 1403428Notes

Reaction equation

HRID 1403428 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.[NH:29]1[C:37]2[C:32](=[CH:33][C:34](B(O)O)=[CH:35][CH:36]=2)[CH:31]=[CH:30]1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].O>O1CCOCC1.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>[NH:29]1[C:37]2[C:32](=[CH:33][C:34]([C:8]3[C:7]([N:1]4[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]4)=[N:16][C:15]4[C:10](=[CH:11][CH:12]=[C:13]([C:17]([O:19][CH3:20])=[O:18])[CH:14]=4)[N:9]=3)=[CH:35][CH:36]=2)[CH:31]=[CH:30]1

Participants

7

Reactant 4

HCID 962WaterHCID 62657Potassium Phosphate, TribasicHCID 27343615-Indolylboronic acidHCID 86670562HCID 86670562, compound

Product 1

HCID 70664762HCID 70664762, compoundYield 33.7%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of methyl 3-(piperidin-1-yl)-2-(trifluoromethylsulfonyloxy)quinoxaline-6-carboxylate (290 mg, crude) in dioxane (5 mL) was added 1H-indol-5-ylboronic acid (337 mg, 2.1 mmol), K3PO4 (443 mg, 2.1 mmol), Pd(PPh3)4 (40 mg, 0.03 mmol) and water (0.5 mL). The resulting solution was stirred for 1 h at 90° C. and then quenched by the addition of CH2Cl2 (100 mL), washed with water (3×50 mL), dried over anhydrous sodium sulfate and concentrated in vacuo to give a residue, which was purified by silica gel column chromatography eluting with 5% ethyl acetate in petroleum ether to afford methyl 2-(1H-indol-5-yl)-3-(piperidin-1-yl)quinoxaline-6-carboxylate as a yellow solid (90.0 mg, 33%).

Workup

  1. customquenched by the addition of CH2Cl2 (100 mL)
  2. washwashed with water (3×50 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customto give a residue, which
  6. customwas purified by silica gel column chromatography
  7. washeluting with 5% ethyl acetate in petroleum ether

Sources & evidence

ORD record
ord-d895dbc8105d47ac9c0913ba8adab076
Source dataset
uspto-grants-2014_12
Patent number
US08912188B2

Reaction notes

Loading…