Dimethylformamide → Soticlestat

HRID 60611ノート

反応式

HRID 60611 の反応式
[CH2:1]([C:8]1([OH:23])[CH2:13][CH2:12][N:11]([C:14]([C:16]2[C:17](Cl)=[N:18][CH:19]=[CH:20][CH:21]=2)=[O:15])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N:24]1[CH:29]=[CH:28][C:27](B(O)O)=[CH:26][CH:25]=1.C(=O)([O-])[O-].[Na+].[Na+].CN(C=O)C>[Cl-].[Na+].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.O>[CH2:1]([C:8]1([OH:23])[CH2:13][CH2:12][N:11]([C:14]([C:16]2[C:17]([C:27]3[CH:28]=[CH:29][N:24]=[CH:25][CH:26]=3)=[N:18][CH:19]=[CH:20][CH:21]=2)=[O:15])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

8

反応物 4

HCID 6228DimethylformamideHCID 10340Sodium CarbonateHCID 2734379(Pyridin-4-yl)boronic acidHCID 86680867(4-Benzyl-4-hydroxypiperidin-1-yl)(2-chloropyridin-3-yl)methanone

生成物 1

HCID 73437845Soticlestat収率 60.2%

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 962Water溶媒HCID 57417360Sodium chloride; water溶媒

反応条件

温度
100 °C

実験手順

A mixture of (4-benzyl-4-hydroxypiperidin-1-yl) (2-chloropyridin-3-yl)methanone (5.0 g), tetrakis(triphenylphosphine)palladium(0) (0.87 g), pyridine-4-boronic acid (2.2 g), sodium carbonate (4.8 g), DMF (50 mL) and water (10 ml) was stirred overnight at 100° C. under a nitrogen atmosphere. To the reaction mixture was added saturated brine, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane) to give the title compound (3.4 g). The compound was crystallized from ethyl acetate/heptane to give the title compound as crystals.

後処理

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane)

出典と根拠

ORDレコード
ord-cd6610d24106429e97200c99e6a31796
出典データセット
uspto-grants-2016_09
特許番号
US09440990B2

反応ノート

読み込み中…