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The production process of (R)-1-(1-(methylsulfonyl)propan-2-yl)-4-(trifluoromethyl)-1H-indole-5-carbonitrile is a complex and multi-step process that involves several chemical reactions and purification steps.
This article will provide a detailed overview of the production process of this compound in the chemical industry.
Step 1: Synthesis of Methyl (1S,2S)-2-[(1S)-1-(difluoromethyl)-2-oxo-1,3-oxazolidin-3-yl]-4,5-dihydroimidazo[1,2-d][1,4]benzoxazepin-9-carboxylate
The synthesis of Methyl (1S,2S)-2-[(1S)-1-(difluoromethyl)-2-oxo-1,3-oxazolidin-3-yl]-4,5-dihydroimidazo[1,2-d][1,4]benzoxazepin-9-carboxylate is the starting point for the synthesis of (R)-1-(1-(methylsulfonyl)propan-2-yl)-4-(trifluoromethyl)-1H-indole-5-carbonitrile.
This compound is synthesized by a series of chemical reactions that involve the condensation of various reagents, followed by oxidation, dehydration, and coupling reactions.
The synthesis of this compound typically involves the following steps:
Step 1.
1: Condensation of Pivalic Acid and 2-Amino-1,3-oxazolidine
The synthesis of Methyl (1S,2S)-2-[(1S)-1-(difluoromethyl)-2-oxo-1,3-oxazolidin-3-yl]-4,5-dihydroimidazo[1,2-d][1,4]benzoxazepin-9-carboxylate begins with the condensation of pivalic acid and 2-amino-1,3-oxazolidine.
This reaction is typically carried out in the presence of a solvent, such as ethanol, and a catalyst, such as hydrochloric acid.
The resulting product is a mixture of the desired compound and other impurities, which must be purified to obtain a pure sample.
Step 1.
2: Condensation of the Pivalic Acid and 2-Amino-1,3-oxazolidine Adduct with 2,2,2-Trifluoro-1,3-oxazolidine
The next step in the synthesis of Methyl (1S,2S)-2-[(1S)-1-(difluoromethyl)-2-oxo-1,3-oxazolidin-3-yl]-4,5-dihydroimidazo[1,2-d][1,4]benzoxazepin-9-carboxylate involves the condensation of the adduct from step 1.
1 with 2,2,2-Trifluoro-1,3-oxazolidine.
This reaction is typically carried out in the presence of a solvent, such as acetonitrile, and a catalyst, such as pyridine.
The resulting product is a mixture of the desired compound and other impurities, which must be purified to obtain a pure sample.
Step 1.
3: Oxidation of the Pivalic Acid and 2,2,2-Trifluoro-1,3-oxazolidine Adduct
The next step in the synthesis of Methyl (1S,2S)-2-[(1S)-1-(difluoromethyl)-2-oxo-1,3-oxazolidin-3-yl]-4,5-dihydroimidazo[1,2-d][1,4]benzoxazepin-9-carboxylate involves the oxidation of the adduct from step 1.
2.
This reaction is typically carried out in the presence of a solvent, such as acetonitrile, and an oxidizing agent, such as t