Dichloromethane methanol ammonium hydroxide → HCID 44317162, compound

HRID 1419149Notes

Reaction equation

HRID 1419149 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]2[CH:11]=[C:12]3[C:16](=[CH:17][CH:18]=2)[NH:15][CH:14]=[C:13]3[CH:19]2[CH2:23][CH2:22][N:21]([CH3:24])[CH2:20]2)=[C:5]([N+:25]([O-])=O)[CH:4]=1)#[N:2].[CH:28](OCC)(OCC)OCC.C(O)=O.C(Cl)Cl.CO.[OH-].[NH4+]>>[C:1]([C:3]1[CH:8]=[CH:7][C:6]2[N:9]([C:10]3[CH:11]=[C:12]4[C:16](=[CH:17][CH:18]=3)[NH:15][CH:14]=[C:13]4[CH:19]3[CH2:23][CH2:22][N:21]([CH3:24])[CH2:20]3)[CH:28]=[N:25][C:5]=2[CH:4]=1)#[N:2]

Participants

4

Reactant 3

HCID 21896990Dichloromethane methanol ammonium hydroxideHCID 54032321HCID 54032321, compoundHCID 86753982HCID 86753982, compound

Product 1

HCID 44317162HCID 44317162, compoundYield 22%

Procedure

5-(4-Cyano-2-nitrophenyl)amino-3-(N-methylpyrrolidin-3-yl)-1H-indole was used. Reduction was by catalytic hydrogenation, the cyclization reaction used triethyl orthoformate/formic acid, and the cyclization reaction was heated for 2 hours. Chromatography using 9:1:0.5 [methylene chloride/methanol/ammonium hydroxide] afforded the title compound (22%) as a light yellow solid: Rf =0.35 in 9:1:0.1 [methylene chloride/methanol/ammonium hydroxide]; 13C NMR (CDCl3) δ 145.7, 143.3, 137.5, 136.5, 127.5, 126.8, 126.7, 125.4, 123.0, 120.3, 119.9, 118.5, 115.8, 112.7, 111.9, 105.7, 62.8, 56.3, 42.3, 35.0, 32.3; FAB LRMS (m/z, relative intensity) 342 (MH+).

Workup

  1. customthe cyclization reaction
  2. customthe cyclization reaction
  3. temperaturewas heated for 2 hours

Sources & evidence

ORD record
ord-bb80c74f668040029ba56182a53a2e5c
Source dataset
uspto-grants-1999_03
Patent number
US05886008

Reaction notes

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