Potassium Phosphate, Tribasic → HCID 60171606, compound

HRID 1405285Notes

Reaction equation

HRID 1405285 reaction equation
[F:1][C:2]1[CH:13]=[CH:12][C:5]2[S:6][C:7](B(O)O)=[CH:8][C:4]=2[CH:3]=1.Cl[C:15]1[C:24]([N:25]([CH:27]([CH3:29])[CH3:28])[CH3:26])=[N:23][C:22]2[C:17](=[CH:18][CH:19]=[C:20]([C:30]([O:32][CH3:33])=[O:31])[CH:21]=2)[N:16]=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>[F:1][C:2]1[CH:13]=[CH:12][C:5]2[S:6][C:7]([C:15]3[C:24]([N:25]([CH:27]([CH3:29])[CH3:28])[CH3:26])=[N:23][C:22]4[C:17](=[CH:18][CH:19]=[C:20]([C:30]([O:32][CH3:33])=[O:31])[CH:21]=4)[N:16]=3)=[CH:8][C:4]=2[CH:3]=1

Participants

7

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 53234193(5-Fluoro-1-benzothiophen-2-yl)boronic acidHCID 86667203Methyl 2-chloro-3-(isopropyl(methyl)amino)quinoxaline-6-carboxylate

Product 1

HCID 60171606HCID 60171606, compoundYield 88.2%

Reagents, catalysts & solvents 3

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

Procedure

To a solution of 5-fluorobenzo[b]thiophen-2-ylboronic acid (202 mg, 1.03 mmol) in dioxane (6 mL) was added methyl 2-chloro-3-(isopropyl(methyl)amino)quinoxaline-6-carboxylate (120 mg, 0.41 mmol), K3PO4 (259 mg, 1.23 mmol), Pd(PPh3)4 (24.0 mg, 0.02 mmol) and water (3 drops) with stifling for 0.5 h at 90° C. in an oil bath with an inert atmosphere of nitrogen. The reaction mixture was concentrated under vacuum and then purified by a silica gel column with 1% to 2% ethyl acetate in petroleum ether to afford methyl 2-(5-fluorobenzo[b]thiophen-2-yl)-3-(isopropyl(methyl)amino)quinoxaline-6-carboxylate as a light yellow solid (148 mg, 88%).

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. custompurified by a silica gel column with 1% to 2% ethyl acetate in petroleum ether

Sources & evidence

ORD record
ord-bf4ea91b544142ff8f6fa0356a9ed187
Source dataset
uspto-grants-2014_12
Patent number
US08916561B2

Reaction notes

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