N-[4-Chloro-2-iodo-5-(trifluoromethyl)phenyl]methanesulfonamide → 2-(5-chloro-1-methanesulfonyl-6-trifluoromethyl-1H-indol-2-yl)-1-(2,2,2-trifluoro-ethylsulfanyl)-butan-2-ol

HRID 55953Notes

Reaction equation

HRID 55953 reaction equation
[Cl:1][C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][C:5]([NH:12][S:13]([CH3:16])(=[O:15])=[O:14])=[C:4](I)[CH:3]=1.[F:18][C:19]([F:30])([F:29])[CH2:20][S:21][CH2:22][C:23]([OH:28])([CH2:26][CH3:27])[C:24]#[CH:25]>>[Cl:1][C:2]1[CH:3]=[C:4]2[C:5](=[CH:6][C:7]=1[C:8]([F:11])([F:10])[F:9])[N:12]([S:13]([CH3:16])(=[O:15])=[O:14])[C:24]([C:23]([OH:28])([CH2:26][CH3:27])[CH2:22][S:21][CH2:20][C:19]([F:30])([F:18])[F:29])=[CH:25]2

Participants

3

Reactant 2

HCID 66864554N-[4-Chloro-2-iodo-5-(trifluoromethyl)phenyl]methanesulfonamideHCID 860800943-(2,2,2-Trifluoro-ethylsulfanylmethyl)-pent-1yn-3-ol

Product 1

HCID 116630592-(5-chloro-1-methanesulfonyl-6-trifluoromethyl-1H-indol-2-yl)-1-(2,2,2-trifluoro-ethylsulfanyl)-butan-2-ol

Procedure

This compound was prepared using the standard Sonagashira procedure as described in General Procedures Example C, reacting from N-(4-chloro-2-iodo-5-trifluoromethyl-phenyl)-methanesulfonamide (0.60 g, 1.5 mmol) and 3-(2,2,2-Trifluoro-ethylsulfanylmethyl)-pent-1yn-3-ol (0.32 g, 1.5 mmol) to yield the title compound as a yellow sticky oil.

Workup

  1. customThis compound was prepared

Sources & evidence

ORD record
ord-b3bcd0e62c59493796e86dfc933a3281
Source dataset
uspto-grants-2016_09
Patent number
US09434688B2

Reaction notes

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