Phenylboronic Acid → HCID 86659953、化合物

HRID 2366060ノート

反応式

HRID 2366060 の反応式
Br[C:2]1[CH:7]=[C:6]([N:8]([CH3:10])[CH3:9])[CH:5]=[CH:4][N:3]=1.[C:11](=[N:24][NH2:25])([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.CC(C)([O-])C.[Na+].C1(B(O)O)C=CC=CC=1>C1(C)C=CC=CC=1.CCOC(C)=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:12]1([C:11]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[N:24][NH:25][C:2]2[CH:7]=[C:6]([N:8]([CH3:10])[CH3:9])[CH:5]=[CH:4][N:3]=2)[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

参加物

8

反応物 4

HCID 66827Phenylboronic AcidHCID 79304DiphenylmethylidenehydrazineHCID 117456782-Bromo-4-(dimethylamino)pyridineHCID 23676156Sodium t-butoxide

生成物 1

HCID 86659953HCID 86659953、化合物

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 1140Toluene溶媒2 回HCID 8857Ethyl Acetate溶媒

反応条件

温度
80 °C

実験手順

To a mixture of 3.3 g (16.41 mmol) of 2-bromo-N,N-dimethylpyridin-4-amine in 40 mL of anhydrous toluene, 3.5 g (18.05 mmol) of benzophenone hydrazone, 2.2 g (23 mmol) of anhydrous sodium tert-butoxide and 100 mg (0.82 mmol) of benzeneboronic acid in 40 mL of toluene are added, under argon, at room temperature, after having degassed the reaction medium under argon, 74 mg (0.33 mmol) of palladium acetate and 205 mg (0.33 mmol) of racBINAP. The reaction medium is then heated for 4 hours at 80° C. The reaction medium is taken up in 200 mL of EtOAc, washed successively with water (3×30 mL), with saturated NaHCO3 solution (30 mL) and with brine (30 mL) and then dried over Na2SO4, filtered and concentrated under reduced pressure. The residue obtained is purified by chromatography on a column of silica gel, eluting with a DCM/MeOH gradient of from 0 to 10% MeOH. After concentrating under reduced pressure, 4.5 g of 2-[2-(diphenylmethylidene)hydrazino]-N,N-dimethylpyridin-4-amine are obtained in the form of a red solid.

後処理

  1. additionare added, under argon, at room temperature
  2. customafter having degassed the reaction medium under argon
  3. washwashed successively with water (3×30 mL), with saturated NaHCO3 solution (30 mL) and with brine (30 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue obtained
  8. customis purified by chromatography on a column of silica gel
  9. washeluting with a DCM/MeOH gradient of from 0 to 10% MeOH
  10. concentrationAfter concentrating under reduced pressure, 4.5 g of 2-[2-(diphenylmethylidene)hydrazino]-N,N-dimethylpyridin-4-amine
  11. customare obtained in the form of a red solid

出典と根拠

ORDレコード
ord-5d60072cc4454a34a18e4cd6c06addd7
出典データセット
uspto-grants-2014_04
特許番号
US08697731B2

反応ノート

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