Water → HCID 70654432, compound

HRID 1405318Notes

Reaction equation

HRID 1405318 reaction equation
Cl[C:2]1[C:11]([N:12]([CH3:16])[CH:13]([CH3:15])[CH3:14])=[N:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:17]#[N:18])[CH:8]=2)[N:3]=1.[CH3:19][C:20]1[NH:21][C:22]2[C:27]([CH:28]=1)=[CH:26][C:25](B1OC(C)(C)C(C)(C)O1)=[CH:24][CH:23]=2.C(=O)([O-])[O-].[K+].[K+].O>COCCOC.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>[CH3:16][N:12]([CH:13]([CH3:15])[CH3:14])[C:11]1[C:2]([C:25]2[CH:26]=[C:27]3[C:22](=[CH:23][CH:24]=2)[NH:21][C:20]([CH3:19])=[CH:28]3)=[N:3][C:4]2[C:9]([N:10]=1)=[CH:8][C:7]([C:17]#[N:18])=[CH:6][CH:5]=2

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 184506482-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)-1H-indoleHCID 86670228HCID 86670228, compound

Product 1

HCID 70654432HCID 70654432, compoundYield 58.6%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 2-chloro-3-[methyl(propan-2-yl)amino]quinoxaline-6-carbonitrile (250 mg, 0.96 mmol) in DME (8 ml) was added 2-methyl-5-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (494 mg, 1.92 mmol), potassium carbonate (265 mg, 1.92 mmol), Pd(PPh3)4 (58 mg, 0.05 mmol) and water (2 ml). The resulting solution was stirred for 1 h at 90° C. under an inert atmosphere of nitrogen. Then the mixture was quenched with water (100 ml) and extracted with ethyl acetate (3×50 ml), and the organic layers combined and dried over anhydrous magnesium sulfate. The filtrate was concentrated in vacuo to give a residue, which was purified via silica gel column chromatography (10%-20% ethyl acetate in petroleum ether) to afford 3-[methyl(propan-2-yl)amino]-2-(2-methyl-1H-indol-5-yl)quinoxaline-6-carbonitrile as a yellow solid (200 mg, 58%).

Workup

  1. customThen the mixture was quenched with water (100 ml)
  2. extractionextracted with ethyl acetate (3×50 ml)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationThe filtrate was concentrated in vacuo
  5. customto give a residue, which
  6. customwas purified via silica gel column chromatography (10%-20% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-41795e79e9da4e9aaac34b7d52123189
Source dataset
uspto-grants-2014_12
Patent number
US08916561B2

Reaction notes

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