Dimethylformamide → 7-(5-Bromopyridin-2-yl)-7-azaspiro[3.5]nonan-2-ol

HRID 336535ノート

反応式

HRID 336535 の反応式
[Br:1][C:2]1[CH:3]=[CH:4][C:5](F)=[N:6][CH:7]=1.Cl.[CH2:10]1[C:13]2([CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)[CH2:12][CH:11]1[OH:19].C(N(CC)C(C)C)(C)C.CN(C=O)C>C(#N)C.C(OCC)(=O)C.O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N:16]2[CH2:17][CH2:18][C:13]3([CH2:10][CH:11]([OH:19])[CH2:12]3)[CH2:14][CH2:15]2)=[N:6][CH:7]=1

参加物

8

反応物 4

HCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 27831685-Bromo-2-fluoropyridineHCID 680015347-Azaspiro[3.5]nonan-2-ol hydrochloride

生成物 1

HCID 680009857-(5-Bromopyridin-2-yl)-7-azaspiro[3.5]nonan-2-ol

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6342Acetonitrile溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
95 °C

実験手順

0.24 g (1.35 mmol) of 5-bromo-2-fluoropyridine, 0.20 g (1.13 mmol) of 7-azaspiro[3.5]nonan-2-ol hydrochloride (JP 2003246780) and 0.51 g (3.94 mmol) of N,N-diisopropylethylamine in 3 mL of acetonitrile are placed in a sealed tube. 1 mL of DMF is added and the mixture is then heated at 95° C. for 12 hours. The reaction mixture is allowed to cool to room temperature and is then taken up in ethyl acetate and water. The aqueous phase is separated out and the combined organic phases are then washed with saturated aqueous ammonium chloride solution and dried over sodium sulfate, and the filtrate is concentrated under reduced pressure. After purification by chromatography on silica gel, eluting with a 95/5/0.5 mixture of dichloromethane, methanol and 28% aqueous ammonia, 0.138 g pure product is thus obtained in the form of a colourless gum.

後処理

  1. temperatureto cool to room temperature
  2. customThe aqueous phase is separated out
  3. washthe combined organic phases are then washed with saturated aqueous ammonium chloride solution
  4. dry with materialdried over sodium sulfate
  5. concentrationthe filtrate is concentrated under reduced pressure
  6. customAfter purification by chromatography on silica gel
  7. washeluting with a 95/5/0.5 mixture of dichloromethane, methanol and 28% aqueous ammonia, 0.138 g pure product
  8. customis thus obtained in the form of a colourless gum

出典と根拠

ORDレコード
ord-344938c8d485402a8ad6a85ab6408f08
出典データセット
uspto-grants-2014_11
特許番号
US08889702B2

反応ノート

読み込み中…