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

HRID 80918ノート

反応式

HRID 80918 の反応式
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]

参加物

6

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
100 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-f75d2e6e2a274443a10f6b15a0c021c6
出典データセット
uspto-grants-2014_09
特許番号
US08846677B2

反応ノート

読み込み中…