Potassium Phosphate, Tribasic → HCID 178497312, compound

HRID 1403382Notes

Reaction equation

HRID 1403382 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.[CH3:21][C:22]1[C:30]2[C:25](=[CH:26][CH:27]=[C:28](B3OC(C)(C)C(C)(C)O3)[CH:29]=2)[NH:24][N:23]=1.[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>[CH:14]([N:12]([CH3:13])[C:11]1[C:2]([C:28]2[CH:29]=[C:30]3[C:25](=[CH:26][CH:27]=2)[NH:24][N:23]=[C:22]3[CH3:21])=[N:3][C:4]2[C:9]([N:10]=1)=[CH:8][C:7]([C:17]([O:19][CH3:20])=[O:18])=[CH:6][CH:5]=2)([CH3:16])[CH3:15]

Participants

7

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 86667203Methyl 2-chloro-3-(isopropyl(methyl)amino)quinoxaline-6-carboxylateHCID 178434223HCID 178434223, compound

Product 1

HCID 178497312HCID 178497312, compoundYield 35.8%

Reagents, catalysts & solvents 3

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

Conditions

Temperature
95 °C

Procedure

To a solution of methyl 2-chloro-3-(isopropyl(methyl)amino)quinoxaline-6-carboxylate (180 mg, 0.61 mmol) in 1,4-dioxane (1 mL) was added 3-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole (440 mg, crude), K3PO4 (360 mg, 1.71 mmol), Pd(PPh3)4 (40 mg, 0.03 mmol) under nitrogen atmosphere. After stirring 4 h at 95° C., the reaction mixture was dissolved in water (50 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 a silica gel column with 0.5% methanol in dichloromethane to afford methyl 3-(isopropyl(methyl)amino)-2-(3-methyl-1H-indazol-5-yl)quinoxaline-6-carboxylate as a light yellow solid (85 mg, 35%).

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 a silica gel column with 0.5% methanol in dichloromethane

Sources & evidence

ORD record
ord-16e7a15119d94837b4e0247cc1af29c3
Source dataset
uspto-grants-2014_12
Patent number
US08912188B2

Reaction notes

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