Potassium Phosphate, Tribasic → methyl 2-(3,4-dihydro-2H-benzo[b][1,4]dioxepin-7-yl)-3-(isopropyl(methyl)amino)quinoxaline-6-carboxylate

HRID 1403344Notes

Reaction equation

HRID 1403344 reaction equation
[O:1]1[CH2:7][CH2:6][CH2:5][O:4][C:3]2[CH:8]=[C:9](B(O)O)[CH:10]=[CH:11][C:2]1=2.Cl[C:16]1[C:25]([N:26]([CH:28]([CH3:30])[CH3:29])[CH3:27])=[N:24][C:23]2[C:18](=[CH:19][CH:20]=[C:21]([C:31]([O:33][CH3:34])=[O:32])[CH:22]=2)[N:17]=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>[O:1]1[CH2:7][CH2:6][CH2:5][O:4][C:3]2[CH:8]=[C:9]([C:16]3[C:25]([N:26]([CH:28]([CH3:30])[CH3:29])[CH3:27])=[N:24][C:23]4[C:18](=[CH:19][CH:20]=[C:21]([C:31]([O:33][CH3:34])=[O:32])[CH:22]=4)[N:17]=3)[CH:10]=[CH:11][C:2]1=2

Participants

7

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 27763983,4-Dihydro-2H-1,5-benzodioxepin-7-ylboronic acidHCID 86667203Methyl 2-chloro-3-(isopropyl(methyl)amino)quinoxaline-6-carboxylate

Product 1

HCID 70664851methyl 2-(3,4-dihydro-2H-benzo[b][1,4]dioxepin-7-yl)-3-(isopropyl(methyl)amino)quinoxaline-6-carboxylateYield 63%

Reagents, catalysts & solvents 3

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

Conditions

Temperature
90 °C

Procedure

To a solution of 3,4-dihydro-2H-benzo[b][1,4]dioxepin-7-ylboronic acid (200.0 mg, 1.03 mmol in dioxane (5.0 mL) was added methyl 2-chloro-3-(isopropyl(methyl)amino)quinoxaline-6-carboxylate (Scheme I, 150.0 mg, 0.52 mmol), K3PO4 (325.9 mg, 1.54 mmol) and Pd(PPh3)4 (29.7 mg, 0.03 mmol) and water (3 drops) with stirring for 1 h at 90° C. in an oil bath maintained with an inert atmosphere of nitrogen. The reaction mixture was concentrated under vacuum to give a residue, which was purified by a silica gel column with 1% ethyl acetate in petroleum ether to afford methyl 2-(3,4-dihydro-2H-benzo[b][1,4]dioxepin-7-yl)-3-(isopropyl(methyl)amino)quinoxaline-6-carboxylate as a light yellow solid (140.0 mg, 63%).

Workup

  1. temperaturemaintained with an inert atmosphere of nitrogen
  2. concentrationThe reaction mixture was concentrated under vacuum
  3. customto give a residue, which
  4. customwas purified by a silica gel column with 1% ethyl acetate in petroleum ether

Sources & evidence

ORD record
ord-56b0271c030647d6999ec7cf756f1fba
Source dataset
uspto-grants-2014_12
Patent number
US08912188B2

Reaction notes

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