Methyl iodide → 5-bromo-N-(5-chlorothiazol-2-yl)-1'-methylspiro[indoline-3,3'-pyrrolidine]-1-carboxamide

HRID 1411238ノート

反応式

HRID 1411238 の反応式
[Br:1][C:2]1[CH:3]=[C:4]2[C:10]3([CH2:14][CH2:13][NH:12][CH2:11]3)[CH2:9][N:8]([C:15]([NH:17][C:18]3[S:19][C:20]([Cl:23])=[CH:21][N:22]=3)=[O:16])[C:5]2=[CH:6][CH:7]=1.[C:24](=O)([O-])[O-].[K+].[K+].CI>CN(C=O)C.O>[Br:1][C:2]1[CH:3]=[C:4]2[C:10]3([CH2:14][CH2:13][N:12]([CH3:24])[CH2:11]3)[CH2:9][N:8]([C:15]([NH:17][C:18]3[S:19][C:20]([Cl:23])=[CH:21][N:22]=3)=[O:16])[C:5]2=[CH:6][CH:7]=1

参加物

6

反応物 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 71522964HCID 71522964、化合物

生成物 1

HCID 904497475-bromo-N-(5-chlorothiazol-2-yl)-1'-methylspiro[indoline-3,3'-pyrrolidine]-1-carboxamide収率 35%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

The 5-bromo-N-(5-chlorothiazol-2-yl)spiro[indoline-3,3′-pyrrolidine]-1-carboxamide (48.2 mg, 0.105 mmol) obtained in Example 2 was dissolved in N,N′-dimethylformamide (1.0 mL). Thereafter, potassium carbonate (43.5 mg, 0.315 mmol) and methyl iodide (30.0 mg, 0.210 mmol) were added to the above obtained solution at room temperature, and the obtained mixture was then stirred for 3 hours. Thereafter, the reaction solution was diluted with water, and was then extracted with methylene chloride. The organic layer was washed with brine, and was then dried over anhydrous sodium sulfate, followed by concentration in vacuo. The obtained residue was purified by silica gel column chromatography (chloroform:methanol=10:1) to obtain the captioned compound (11.0 mg, 35%) in the form of a white solid.

後処理

  1. extractionwas then extracted with methylene chloride
  2. washThe organic layer was washed with brine
  3. dry with materialwas then dried over anhydrous sodium sulfate
  4. concentrationfollowed by concentration in vacuo
  5. customThe obtained residue was purified by silica gel column chromatography (chloroform:methanol=10:1)

出典と根拠

ORDレコード
ord-9f844f6c2ea6492bae8807416674da96
出典データセット
uspto-grants-2014_12
特許番号
US08921576B2

反応ノート

読み込み中…