Phenyl dihydrogen orthoborate → HCID 57514566, compound

HRID 1924409Notes

Reaction equation

HRID 1924409 reaction equation
Br[C:2]1[CH:11]=[C:10]([CH3:12])[CH:9]=[C:8]2[C:3]=1[N:4]=[CH:5][CH:6]=[N:7]2.[C:13]1(OB(O)O)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>O1CCOCC1.CO.C(=O)([O-])[O-].[Na+].[Na+].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>[CH3:12][C:10]1[CH:9]=[C:8]2[C:3]([N:4]=[CH:5][CH:6]=[N:7]2)=[C:2]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:11]=1

Participants

7

Reactant 2

HCID 78412Phenyl dihydrogen orthoborateHCID 45117463Quinoxaline, 5-bromo-7-methyl- (9CI)

Product 1

HCID 57514566HCID 57514566, compound

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 887MethanolSolventHCID 10340Sodium CarbonateSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 400 mg of 5-bromo-7-methyl-quinoxaline, 244 mg of phenylboric acid and 100 mg of tetrakis(triphenylphosphine)palladium in 12 ml dioxane, 4 ml of methanol and 3.6 ml 1 M aqueous sodium carbonate solution is refluxed for three hours under an argon atmosphere. Then the reaction mixture is evaporated down and the residue is distributed between ethyl acetate and water. The ethyl acetate phase is separated off, dried over magnesium sulphate and evaporated down. The crude product is purified by chromatography over a silica gel column with cyclohexane/ethyl acetate (85:15 to 70:30) as eluant.

Workup

  1. temperatureis refluxed for three hours under an argon atmosphere
  2. customThen the reaction mixture is evaporated down
  3. customThe ethyl acetate phase is separated off
  4. dry with materialdried over magnesium sulphate
  5. customevaporated down
  6. customThe crude product is purified by chromatography over a silica gel column with cyclohexane/ethyl acetate (85:15 to 70:30) as eluant

Sources & evidence

ORD record
ord-9e77c101110941908718351c6a5c8e1f
Source dataset
uspto-grants-2012_05
Patent number
US08178541B2

Reaction notes

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