5-Aminoindole → HCID 9946084, compound

HRID 1595796Notes

Reaction equation

HRID 1595796 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:16]#[N:17].[NH2:18][C:19]1[CH:20]=[C:21]2[C:25](=[CH:26][CH:27]=1)[NH:24][CH:23]=[CH:22]2.Cl.N1C=CC=CC=1>C(OCCO)C>[NH:24]1[C:25]2[C:21](=[CH:20][C:19]([NH:18][C:2]3[C:11]4[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=4)[N:5]=[CH:4][C:3]=3[C:16]#[N:17])=[CH:27][CH:26]=2)[CH:22]=[CH:23]1

Participants

5

Reactant 3

HCID 788675-AminoindoleHCID 10176127Pyridinium chlorideHCID 105866764-Chloro-6,7-dimethoxy-quinoline-3-carbonitrile

Product 1

HCID 9946084HCID 9946084, compound

Reagents, catalysts & solvents 1

HCID 8076Glycol monoethyl etherSolvent

Procedure

Using an analogous procedure to that described in Example 141, 248.7 mg (1 mmol) of 4-chloro-6,7-dimethoxy-3-quinolinecarbonitrile, 158.6 mg (1.2 mmol) of 5-aminoindole and 115.6 mg (1 mmol) of pyridine hydrochloride in 10 mL of 2-ethoxyethanol was refluxed for 0.5 hr. The work up gave 338.7 mg (98.5%) of the product as a yellow solid, m.p.>250° C., mass (electrospray, m/e): M+H 344.9. HRCIMS: calcd 344.127 for C20H16N4O2 (M+), obsd 344.1277.

Workup

  1. temperaturewas refluxed for 0.5 hr

Sources & evidence

ORD record
ord-1a2775c5d535493fb8b5f0fb946f3ba5
Source dataset
uspto-grants-2001_09
Patent number
US06288082B1

Reaction notes

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