Potassium Phosphate, Tribasic → HCID 70664817, compound

HRID 1403306

Reaction equation

HRID 1403306 reaction equation
Cl[C:2]1[C:11]([N:12]([CH:14]([CH3:16])[CH3:15])[CH3:13])=[N:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:17]([O:19][CH3:20])=[O:18])[CH:8]=2)[N:3]=1.[C:21]([O:25][C:26]([N:28]1[C:36]2[C:31](=[CH:32][C:33]([O:37][CH3:38])=[CH:34][CH:35]=2)[CH:30]=[C:29]1B(O)O)=[O:27])([CH3:24])([CH3:23])[CH3:22].[O-]P([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.ClCCl.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>[C:21]([O:25][C:26]([N:28]1[C:36]2[C:31](=[CH:32][C:33]([O:37][CH3:38])=[CH:34][CH:35]=2)[CH:30]=[C:29]1[C:2]1[C:11]([N:12]([CH:14]([CH3:16])[CH3:15])[CH3:13])=[N:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:17]([O:19][CH3:20])=[O:18])[CH:8]=2)[N:3]=1)=[O:27])([CH3:24])([CH3:23])[CH3:22]

Participants

7

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 27947161-Boc-5-methoxyindole-2-boronic acidHCID 86667203Methyl 2-chloro-3-(isopropyl(methyl)amino)quinoxaline-6-carboxylate

Product 1

HCID 70664817HCID 70664817, compoundYield 81.6%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of methyl 2-chloro-3-(isopropyl(methyl)amino)quinoxaline-6-carboxylate (200.0 mg, 0.68 mmol) in 1,4-dioxane (1 mL) was added 1-(tert-butoxycarbonyl)-5-methoxy-1H-indol-2-ylboronic acid (320.0 mg, 1.40 mmol), K3PO4 (440.0 mg, 2.08 mmol), Pd(PPh3)4 (40.0 mg, 0.03 mmol) under nitrogen atmosphere. After stirring 1 h at 90° C., the reaction mixture was dissolved in dichloromethane (50 mL), washed with water (3×20 mL), dried over anhydrous magnesium sulfate and concentrated under reduced pressure to afford a residue, which was purified by a silica gel column with 0.1%-1% ethyl acetate in petroleum ether to afford methyl 2-(1-(tert-butoxycarbonyl)-5-methoxy-1H-indol-2-yl)-3-(isopropyl(methyl)amino)quinoxaline-6-carboxylate as a light yellow solid (280.0 mg, 81%).

Workup

  1. washwashed with water (3×20 mL)
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customto afford a residue, which
  5. customwas purified by a silica gel column with 0.1%-1% ethyl acetate in petroleum ether

Sources & evidence

ORD record
ord-931efa1a66284463b407087c341caada
Source dataset
uspto-grants-2014_12
Patent number
US08912188B2

Linked notes

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