Methanesulfonyl chloride → N-(2-Butyl-1-benzofuran-5-yl)methanesulfonamide
Reaction equation
[CH2:1]([C:5]1[O:6][C:7]2[CH:13]=[CH:12][C:11]([NH2:14])=[CH:10][C:8]=2[CH:9]=1)[CH2:2][CH2:3][CH3:4].[CH3:15][S:16](Cl)(=[O:18])=[O:17]>>[CH2:1]([C:5]1[O:6][C:7]2[CH:13]=[CH:12][C:11]([NH:14][S:16]([CH3:15])(=[O:18])=[O:17])=[CH:10][C:8]=2[CH:9]=1)[CH2:2][CH2:3][CH3:4]Participants
3
Procedure
A process for synthesizing dronedarone was described in patent application WO 02/48132, mentioned previously, using 2-n-butyl-5-nitrobenzofuran, which is reduced, under pressure with hydrogen in the presence of platinum oxide as catalyst to form 2-n-butyl-5-aminobenzofuran. This benzofuran derivative is then subjected to the action of methanesulfonyl chloride, which gives 2-n-butyl-5-methanesulfonamidobenzofuran, which is treated with 4-[3-(di-n-butylamino)propoxy]benzoyl chloride to obtain dronedarone.
Sources & evidence
- ORD record
- ord-57633d4d2f8647329a5d02157df701e5
- Source dataset
- uspto-grants-2016_05
- Patent number
- US09334254B2
Reaction notes
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