Cesium carbonate → 3-Cyclopropyl-2-fluoro-5-nitroaniline

HRID 710214

反応式

HRID 710214 の反応式
Br[C:2]1[C:3]([F:12])=[C:4]([CH:6]=[C:7]([N+:9]([O-:11])=[O:10])[CH:8]=1)[NH2:5].B1([CH:24]2[CH2:26][CH2:25]2)OC(=O)CN(C)CC(=O)O1.P(C1CCCCC1)(C1CCCCC1)C1CCCCC1.C([O-])([O-])=O.[Cs+].[Cs+]>C1(C)C=CC=CC=1.O.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH:24]1([C:2]2[C:3]([F:12])=[C:4]([CH:6]=[C:7]([N+:9]([O-:11])=[O:10])[CH:8]=2)[NH2:5])[CH2:26][CH2:25]1

参加物

7

反応物 4

HCID 10796Cesium carbonateHCID 75806TricyclohexylphosphineHCID 441383422-Cyclopropyl-6-methyl-1,3,6,2-dioxazaborocane-4,8-dioneHCID 580658073-Bromo-2-fluoro-5-nitroaniline

生成物 1

HCID 580658083-Cyclopropyl-2-fluoro-5-nitroaniline収率 69.2%

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 22272177Toluene water溶媒

反応条件

温度
100 °C

実験手順

A mixture of 3-bromo-2-fluoro-5-nitroaniline (2.20 g, 9.36 mmol, 1 equiv), cyclopropylboronic acid MIDA ester (Aldrich; 11.07 g, 56.17 mmol, 6 equiv), Cy3P (1.05 g, 3.74 mmol, 0.4 equiv), Cs2CO3 (54.90 g, 168.50 mmol, 18 equiv) in toluene/H2O (5:1; 450 mL:90 mL) followed by Pd(OAc)2 (0.420 g, 1.87 mmol. 0.20 equiv) was de-gassed by sonicating under vacuum for 10 minutes and back-filled with N2. The mixture was then heated at 100° C. overnight. After allowing to cool to room temperature, the mixture was concentrated to dryness. The residue was taken in DCM, and silica gel was added at this stage so that the residue was absorbed directly on to silica gel. After removing the solvent under vacuum, the crude product was purified by column chromatography on silica gel using DCM to give the product 3-cyclopropyl-2-fluoro-5-nitroaniline (1.27 g, 69%) as a yellow solid.

後処理

  1. customwas de-gassed
  2. customby sonicating under vacuum for 10 minutes
  3. additionback-filled with N2
  4. temperatureto cool to room temperature
  5. concentrationthe mixture was concentrated to dryness
  6. additionsilica gel was added at this stage so that the residue
  7. customwas absorbed directly on to silica gel
  8. customAfter removing the solvent under vacuum
  9. customthe crude product was purified by column chromatography on silica gel

出典と根拠

ORDレコード
ord-57f0a91f5ec24e2f81ca8139a28c13a1
出典データセット
uspto-grants-2015_11
特許番号
US09181222B2

関連ノート

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