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

HRID 1098916Notes

Reaction equation

HRID 1098916 reaction equation
[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

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 8008ButyronitrileSolvent

Procedure

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%)

Workup

  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

Sources & evidence

ORD record
ord-b4a294ed57724dc3aceac2551afd7a09
Source dataset
uspto-grants-2012_03
Patent number
US08143290B2

Reaction notes

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