Potassium Carbonate → (2-Fluoro-benzyl)-[3-(3-thieno[2,3-d]isoxazol-3-yl-phenoxy)-propyl]-amine

HRID 8644

反応式

HRID 8644 の反応式
Br[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]([C:12]2[C:16]3[S:17][CH:18]=[CH:19][C:15]=3[O:14][N:13]=2)[CH:9]=[CH:10][CH:11]=1.ClCCCOC1C=C(C2C3SC=CC=3ON=2)C=CC=1.[F:39][C:40]1[CH:47]=[CH:46][CH:45]=[CH:44][C:41]=1[CH2:42][NH2:43].C(=O)([O-])[O-].[K+].[K+]>C(#N)C.O>[F:39][C:40]1[CH:47]=[CH:46][CH:45]=[CH:44][C:41]=1[CH2:42][NH:43][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([C:12]2[C:16]3[S:17][CH:18]=[CH:19][C:15]=3[O:14][N:13]=2)[CH:7]=1

参加物

6

反応物 4

HCID 11430Potassium CarbonateHCID 666492-FluorobenzylamineHCID 219835563-[3-(3-Chloro-propoxy)-phenyl]-thieno[2,3-d]isoxazoleHCID 219835593-[3-(3-Bromo-propoxy)phenyl]-thieno[2,3-d]isoxazole

生成物 1

HCID 21983554(2-Fluoro-benzyl)-[3-(3-thieno[2,3-d]isoxazol-3-yl-phenoxy)-propyl]-amine収率 94.1%

試薬・触媒・溶媒 1

HCID 18373917Acetonitrile--water (1/1)溶媒

反応条件

温度
80 °C

実験手順

Combine a mixture (1 mmol total) of 3-[3-(3-bromo-propoxy)-phenyl]-thieno[2,3-d]isoxazole, 3-[3-(3-chloro-propoxy)-phenyl]-thieno[2,3-d]isoxazole with 2-fluorobenzylamine (0.63 g, 5.0 mmol), potassium carbonate (0.41 g, 3.0 mmol) and a mixture of acetonitrile:water (80:20) and heat (80° C.) for 30 hours. Cool the reaction mixture and concentrate to give a residue. Purify the residue by column (silica) chromatography (ethyl acetate). Combine the appropriate fractions and concentrate to give the title compound (0.36 g, 94% Yield) as an oil. Purity by LC/MS (APCI)=100% area, [M+H]+=383 g/mol.

後処理

  1. temperatureCool the reaction mixture
  2. concentrationconcentrate
  3. customto give a residue
  4. customPurify the residue by column (silica) chromatography (ethyl acetate)
  5. concentrationCombine the appropriate fractions and concentrate

出典と根拠

ORDレコード
ord-7618583492454d46a32c9c9120713d00
出典データセット
uspto-grants-2006_08
特許番号
US07091199B1

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