4-Bromoaniline → 4-(1-isobutyl-1H-pyrazol-4-yl)aniline

HRID 873568ノート

反応式

HRID 873568 の反応式
Br[C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.[CH2:9]([N:13]1[CH:17]=[C:16](B2OC(C)(C)C(C)(C)O2)[CH:15]=[N:14]1)[CH:10]([CH3:12])[CH3:11].C(=O)([O-])[O-].[Na+].[Na+]>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].ClCCl.O1CCCC1.CO.O>[CH2:9]([N:13]1[CH:17]=[C:16]([C:2]2[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=2)[CH:15]=[N:14]1)[CH:10]([CH3:12])[CH3:11]

参加物

6

反応物 3

HCID 78074-BromoanilineHCID 10340Sodium CarbonateHCID 27593921-Isobutyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

生成物 1

HCID 633283934-(1-isobutyl-1H-pyrazol-4-yl)aniline

試薬・触媒・溶媒 2

HCID 178418807HCID 178418807、化合物触媒HCID 21892291Methanol tetrahydrofuran water溶媒

反応条件

温度
85 °C

実験手順

A suspension of 4-bromoaniline (406 mg, 2.362 mmol), 1-isobutyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (650 mg, 2.60 mmol), PdCl2(dppf)-dichloromethane adduct (57.9 mg, 0.071 mmol) and sodium carbonate (526 mg, 4.96 mmol) in a 6:2:1 mixture of tetrahydrofuran/methanol/water (12 ml) was taken through three vacuum/nitrogen purge cycles; and the reaction mixture was heated in an oil bath at 85° C. overnight. The mixture was diluted with ethyl acetate and water; the separated aqueous layer was extracted with ethyl acetate and the combined organic layers were washed with brine, dried with magnesium sulfate, filtered and concentrated. The residue was purified by normal phase chromatography to give the title compound.

後処理

  1. custompurge cycles
  2. additionThe mixture was diluted with ethyl acetate and water
  3. extractionthe separated aqueous layer was extracted with ethyl acetate
  4. washthe combined organic layers were washed with brine
  5. dry with materialdried with magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by normal phase chromatography

出典と根拠

ORDレコード
ord-17f19f6eeb524441b70562349a4e2f84
出典データセット
uspto-grants-2015_03
特許番号
US08975398B2

反応ノート

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