Potassium Phosphate, Tribasic → (S)-methyl 2-(2-methyl-1H-indol-5-yl)-3-(2-methyl-4-(pyridin-2-yl)piperazin-1-yl)quinoxaline-6-carboxylate

HRID 1403538Notes

Reaction equation

HRID 1403538 reaction equation
Br[C:2]1[C:11]([N:12]2[CH2:17][CH2:16][N:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=3)[CH2:14][C@@H:13]2[CH3:24])=[N:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:25]([O:27][CH3:28])=[O:26])[CH:8]=2)[N:3]=1.[CH3:29][C:30]1[NH:31][C:32]2[C:37]([CH:38]=1)=[CH:36][C:35](B1OC(C)(C)C(C)(C)O1)=[CH:34][CH:33]=2.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>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>[CH3:29][C:30]1[NH:31][C:32]2[C:37]([CH:38]=1)=[CH:36][C:35]([C:2]1[C:11]([N:12]3[CH2:17][CH2:16][N:15]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=4)[CH2:14][C@@H:13]3[CH3:24])=[N:10][C:9]3[C:4](=[CH:5][CH:6]=[C:7]([C:25]([O:27][CH3:28])=[O:26])[CH:8]=3)[N:3]=1)=[CH:34][CH:33]=2

Participants

6

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 184506482-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)-1H-indoleHCID 86670576(S)-methyl 2-bromo-3-(2-methyl-4-(pyridin-2-yl)piperazin-1-yl)quinoxaline-6-carboxylate

Product 1

HCID 70664686(S)-methyl 2-(2-methyl-1H-indol-5-yl)-3-(2-methyl-4-(pyridin-2-yl)piperazin-1-yl)quinoxaline-6-carboxylateYield 91.1%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of (S)-methyl 2-bromo-3-(2-methyl-4-(pyridin-2-yl)piperazin-1-yl)quinoxaline-6-carboxylate (200 mg, 0.45 mmol) in dioxane (7 ml) was added 2-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (140 mg, 0.54 mmol), K3PO4 (190 mg, 0.90 mmol), and Pd(PPh3)4 (26 mg, 0.02 mmol). The resulting solution was stirred for 2 h at 90° C. Then the mixture was concentrated under vacuum, and the residue was purified via silica gel column chromatography (5% ethyl acetate in petroleum ether) to afford (S)-methyl 2-(2-methyl-1H-indol-5-yl)-3-(2-methyl-4-(pyridin-2-yl)piperazin-1-yl)quinoxaline-6-carboxylate as a yellow solid (202 mg, 91%).

Workup

  1. concentrationThen the mixture was concentrated under vacuum
  2. customthe residue was purified via silica gel column chromatography (5% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-b9dd68de5e044be9aab23e8ef4841ff6
Source dataset
uspto-grants-2014_12
Patent number
US08912188B2

Reaction notes

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