4-Aminophenol → 4-(3-Morpholinopyridin-2-yloxy)benzenamine

HRID 410184ノート

反応式

HRID 410184 の反応式
F[C:2]1[C:7]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)=[CH:6][CH:5]=[CH:4][N:3]=1.[NH2:14][C:15]1[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CS(C)=O>[O:11]1[CH2:12][CH2:13][N:8]([C:7]2[C:2]([O:21][C:18]3[CH:19]=[CH:20][C:15]([NH2:14])=[CH:16][CH:17]=3)=[N:3][CH:4]=[CH:5][CH:6]=2)[CH2:9][CH2:10]1

参加物

5

反応物 3

HCID 4034-AminophenolHCID 10796Cesium carbonateHCID 585476984-(2-Fluoropyridin-3-yl)morpholine

生成物 1

HCID 593272124-(3-Morpholinopyridin-2-yloxy)benzenamine

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
120 °C

実験手順

To a 25 mL round-bottomed flask were added 4-(2-fluoropyridin-3-yl)morpholine (0.523 g, 2.87 mmol), 4-aminophenol (0.451 g, 2.88 mmol), cesium carbonate (1.18 g, 3.45 mmol) and DMSO (5 mL). The reaction mixture was heated at 120° C. for 8 h. After cooling to room temperature, the reaction mixture was filtered through SCX cartridges, and rinsed with DCM, MeOH, and 2.0 ammonia in MeOH. The ammonia rinses were combined and concentrated. The crude product was adsorbed onto a plug of silica gel and chromatographed through a Biotage pre-packed silica gel column (40M), eluting with a gradient of 1% to 5% MeOH in CH2Cl2, to provide 4-(3-morpholinopyridin-2-yloxy)benzenamine. MS: [M+1]=272.1

後処理

  1. temperatureAfter cooling to room temperature
  2. filtrationthe reaction mixture was filtered through SCX cartridges
  3. washrinsed with DCM, MeOH, and 2.0 ammonia in MeOH
  4. concentrationconcentrated
  5. customchromatographed through a Biotage pre-packed silica gel column (40M)
  6. washeluting with a gradient of 1% to 5% MeOH in CH2Cl2

出典と根拠

ORDレコード
ord-3ad3bf63cf5f4127afdc176013080045
出典データセット
uspto-grants-2014_06
特許番号
US08759532B2

反応ノート

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