Isopropenylacetylene → 2-Isopropenyl-1-methanesulfonyl-5-nitro-6-trifluoromethyl-1H-indole

HRID 646559Notes

Reaction equation

I[C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[C:5]([C:11]([F:14])([F:13])[F:12])=[CH:4][C:3]=1[NH:15][S:16]([CH3:19])(=[O:18])=[O:17].[CH3:20][C:21]([C:23]#[CH:24])=[CH2:22]>>[C:21]([C:23]1[N:15]([S:16]([CH3:19])(=[O:18])=[O:17])[C:3]2[C:2]([CH:24]=1)=[CH:7][C:6]([N+:8]([O-:10])=[O:9])=[C:5]([C:11]([F:14])([F:13])[F:12])[CH:4]=2)([CH3:22])=[CH2:20]

Participants

Reactant 2

HCID 62323Isopropenylacetylene

HCID 58979620N-[2-Iodo-4-nitro-5-(trifluoromethyl)phenyl]methanesulfonamide

Product 1

HCID 589795922-Isopropenyl-1-methanesulfonyl-5-nitro-6-trifluoromethyl-1H-indole

Procedure

This compound was prepared using the general Sonagashira conditions as described in general Example C, starting from N-(2-iodo-4-nitro-5-trifluoromethyl-phenyl)-methanesulfonamide (9.0 g, 21.9 mmol) and 2-methyl-1-buten-3-yne (6.25 mL, 65.7 mmol) to yield the title compound as a reddish-brown solid.

Workup

customThis compound was prepared

Sources & evidence

ORD record: ord-517d3eee5a5449fdb8b6bc698e8009fe
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07705147B2

Reaction notes

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