Ethynylcyclohexane → 2-cyclohexyl-5-methyl-7-nitro-1H-indole

HRID 1802807Notes

Reaction equation

I[C:2]1[C:7]([NH2:8])=[C:6]([N+:9]([O-:11])=[O:10])[CH:5]=[C:4]([CH3:12])[CH:3]=1.[CH:13]1([C:19]#[CH:20])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1>>[CH:13]1([C:19]2[NH:8][C:7]3[C:2]([CH:20]=2)=[CH:3][C:4]([CH3:12])=[CH:5][C:6]=3[N+:9]([O-:11])=[O:10])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1

Participants

Reactant 2

HCID 70263Ethynylcyclohexane

HCID 197351992-Iodo-4-methyl-6-nitroaniline

Product 1

HCID 686343312-cyclohexyl-5-methyl-7-nitro-1H-indoleYield 62.4%

Procedure

6-Iodo-4-methyl-2-nitroaniline (500 mg, 1.8 mmol) and cyclohexylacetylene (0.23 ml, 1.8 mmol) were reacted according to the same procedure as Preparation 19 to give the title compound (290 mg, Yield 62%).

Workup

customaccording to the same procedure as Preparation 19

Sources & evidence

ORD record: ord-757b1467e67e408fb9f30e363d61e28a
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08349885B2

Reaction notes

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