5-Aminoindole → 4-(1H-indol-5-ylamino)-7-methoxy-quinoline-3-carbonitrile

HRID 1595793Notes

Reaction equation

HRID 1595793 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:12][CH3:13])=[CH:9][CH:10]=2)[N:5]=[CH:4][C:3]=1[C:14]#[N:15].[NH2:16][C:17]1[CH:18]=[C:19]2[C:23](=[CH:24][CH:25]=1)[NH:22][CH:21]=[CH:20]2>C(OCCO)C>[NH:22]1[C:23]2[C:19](=[CH:18][C:17]([NH:16][C:2]3[C:11]4[C:6](=[CH:7][C:8]([O:12][CH3:13])=[CH:9][CH:10]=4)[N:5]=[CH:4][C:3]=3[C:14]#[N:15])=[CH:25][CH:24]=2)[CH:20]=[CH:21]1

Participants

4

Reactant 2

HCID 788675-Aminoindole2×HCID 125594314-Chloro-7-methoxyquinoline-3-carbonitrile

Product 1

HCID 99446694-(1H-indol-5-ylamino)-7-methoxy-quinoline-3-carbonitrile

Reagents, catalysts & solvents 1

HCID 8076Glycol monoethyl etherSolvent

Conditions

Temperature
120 °C

Procedure

Using an analogous procedure to that described in Example 141, 1.0 g (4.57 mmol) of 4-chloro-7-methoxy-3-quinolinecarbonitrile, 724.8 mg (5.48 mmol) of 5-aminoindole and 528.3 mg (4.57 mmol) of 5-aminoindole in 35 mL of 2-ethoxyethanol was heated at 120° C. for 2 hr. The work up gave 1.38 g of the product as a greenish gray solid, m.p.>250° C., mass (electrospray, m/e): M+H 314.9 HRCIMS: calcd 314.117 for C19H14N4O (M+), obsd 314.1135.

Sources & evidence

ORD record
ord-0409e9929cf54dc4a690dff177765265
Source dataset
uspto-grants-2001_09
Patent number
US06288082B1

Reaction notes

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