(3-Acetamidophenyl)boronic acid → N-{3-[6-(4-Isopropylpiperazin-1-yl)-4-methylpyridin-3-yl]phenyl}acetamide

HRID 80918

Reaction equation

HRID 80918 reaction equation
Br[C:2]1[C:3]([CH3:17])=[CH:4][C:5]([N:8]2[CH2:13][CH2:12][N:11]([CH:14]([CH3:16])[CH3:15])[CH2:10][CH2:9]2)=[N:6][CH:7]=1.[C:18]([NH:21][C:22]1[CH:23]=[C:24](B(O)O)[CH:25]=[CH:26][CH:27]=1)(=[O:20])[CH3:19]>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>[CH:14]([N:11]1[CH2:12][CH2:13][N:8]([C:5]2[N:6]=[CH:7][C:2]([C:26]3[CH:27]=[C:22]([NH:21][C:18](=[O:20])[CH3:19])[CH:23]=[CH:24][CH:25]=3)=[C:3]([CH3:17])[CH:4]=2)[CH2:9][CH2:10]1)([CH3:16])[CH3:15]

Participants

6

Reactant 2

HCID 157274(3-Acetamidophenyl)boronic acidHCID 580066171-(5-Bromo-4-methyl-pyridin-2-yl)-4-isopropyl-piperazine

Product 1

HCID 15951458N-{3-[6-(4-Isopropylpiperazin-1-yl)-4-methylpyridin-3-yl]phenyl}acetamide

Reagents, catalysts & solvents 3

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

Conditions

Temperature
100 °C

Procedure

To a solution of 1-(5-bromo-4-methyl-pyridin-2-yl)-4-isopropyl-piperazine (0.59 g, 2 mmol) in 1,4-dioxane (12 mL) and water (3 mL) was added 3-acetylamino-phenylboronic acid (430 mg, 2.4 mmol), Pd(PPh3)4 (231 mg, 0.2 mmol) and TEA (404 mg, 4 mmol). The resulting mixture was degassed and heated at 100° C. for 4 h under a nitrogen atmosphere. The mixture was diluted with EtOAc and water. The organic layer was separated and the aqueous phase was extracted with EtOAc. The combined organic layers were washed with brine, dried (Na2SO4), concentrated and purified by chromatography on silica gel eluting with CH2Cl2/MeOH (100:1). This afforded 138 mg (15%) of the title compound.

Workup

  1. customThe resulting mixture was degassed
  2. additionThe mixture was diluted with EtOAc and water
  3. customThe organic layer was separated
  4. extractionthe aqueous phase was extracted with EtOAc
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated
  8. custompurified by chromatography on silica gel eluting with CH2Cl2/MeOH (100:1)

Sources & evidence

ORD record
ord-f75d2e6e2a274443a10f6b15a0c021c6
Source dataset
uspto-grants-2014_09
Patent number
US08846677B2

Linked notes

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