Triethylamine → HCID 21474197, compound

HRID 2294166Notes

Reaction equation

[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2.F[C:12]1[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][C:13]=1[N+:19]([O-:21])=[O:20].C(N(CC)CC)C>>[CH3:18][C:15]1[CH:16]=[CH:17][C:12]([NH:1][C:2]2[CH:3]=[C:4]3[C:8](=[CH:9][CH:10]=2)[NH:7][CH:6]=[CH:5]3)=[C:13]([N+:19]([O-:21])=[O:20])[CH:14]=1

Participants

Reactant 3

HCID 8471Triethylamine

HCID 788675-Aminoindole

HCID 1362874-Fluoro-3-nitrotoluene2×

Product 1

HCID 21474197HCID 21474197, compoundYield 90%

Conditions

Temperature: 225 °C

Procedure

5-Aminoindole (0.264 g, 2.00 mmoles) and 4-fluoro-3-nitrotoluene (0.465 g, 3.00 mmoles) were combined with triethylamine (0.42 ml, 3.01 mmoles) in which 4-fluoro-3-nitrotoluene was the only solvent and the reaction was heated at 225° C. under nitrogen for 18 hours. Chromatography using ether/hexanes [1:1 ] afforded the title compound (90%) as a red amorphous solid. Mp, decomposes 94° C.; Rf =0.55 in ethyl acetate/hexanes [1:1]; 13C NMR (CDCl3) δ143.4, 137.3, 134.2, 131.8, 131.1, 128.7, 126.1, 125.6, 120.8, 117.9, 116.2, 112.1, 102.8, 20.1; LRMS (m/z, relative intensity) 267 (M+, 45), 250 (5), 233 (20), 220 (13). HRMS calculated for C15H13N3O2 : 267.1005. Found: 267.0993.

Sources & evidence

ORD record: ord-69c00093d7c242b8bf2eda63f18016e7
Source dataset: uspto-grants-1997_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05688809

Reaction notes

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