Cesium carbonate → (1R,2S)-1-(1-(4-chlorophenyl)-1H-indazol-5-yloxy)-1-(3-methoxyphenyl)propan-2-amine

HRID 13155

反応式

HRID 13155 の反応式
[NH2:1][C@@H:2]([CH3:13])[C@@H:3]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH3:12])[CH:6]=1)[OH:4].[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([N:21]2[C:29]3[C:24](=[CH:25][C:26](I)=[CH:27][CH:28]=3)[CH:23]=[N:22]2)=[CH:17][CH:16]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)CCC.[Cu]I>[Cl:14][C:15]1[CH:16]=[CH:17][C:18]([N:21]2[C:29]3[C:24](=[CH:25][C:26]([O:4][C@H:3]([C:5]4[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH3:12])[CH:6]=4)[C@@H:2]([NH2:1])[CH3:13])=[CH:27][CH:28]=3)[CH:23]=[N:22]2)=[CH:19][CH:20]=1

参加物

6

反応物 3

HCID 10796Cesium carbonateHCID 28743837(1R,2S)-2-Amino-1-(3-methoxyphenyl)-1-propanolHCID 593397541-(4-chlorophenyl)-5-iodo-1H-indazole

生成物 1

HCID 59339670(1R,2S)-1-(1-(4-chlorophenyl)-1H-indazol-5-yloxy)-1-(3-methoxyphenyl)propan-2-amine

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 8008Butyronitrile溶媒

実験手順

The subtitle compound was prepared analogous to the method described in Example 6 (step 6a). Starting from the hydrochloride salt of (1R,2S)-2-amino-1-(3-methoxyphenyl)propan-1-ol (6b) (0.88 g, 4.04 mmol), 1-(4-chlorophenyl)-5-iodo-1H-indazole (1.720 g, 4.85 mmol), CuI (0.154 g, 0.81 mmol) and cesium carbonate (3.95 g, 12.13 mmol) in butyronitrile (14 mL) stirred at +110° C. for 16 h. Work up and final purification by HPLC was followed by extraction of product into EtOAc from basic water solution, evaporation of solvents gave the subtitle compound as a sticky oil. Yield 490 mg (29%)

後処理

  1. customThe subtitle compound was prepared analogous to the method
  2. customfinal purification by HPLC
  3. extractionwas followed by extraction of product into EtOAc from basic water solution, evaporation of solvents

出典と根拠

ORDレコード
ord-a33657903a8b403980a87d7a1a8d5057
出典データセット
uspto-grants-2010_06
特許番号
US07728030B2

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