Water → HCID 22324310, compound

HRID 583816Notes

Reaction equation

HRID 583816 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[CH:7]2)([O-])=O.Cl.Cl[C:15]1[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=1.CC(C)([O-])C.[K+].O>CN(C=O)C>[N:18]1[CH:19]=[CH:20][C:15]([N:9]2[C:10]3[C:6](=[CH:5][C:4]([NH2:1])=[CH:12][CH:11]=3)[CH:7]=[CH:8]2)=[CH:16][CH:17]=1

Participants

6

Reactant 4

HCID 962WaterHCID 225235-NitroindoleHCID 818524-Chloropyridine hydrochlorideHCID 23665647Potassium tert-butoxide

Product 1

HCID 22324310HCID 22324310, compoundYield 58.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 5-nitroindole (7.0 g, 43.2 mmol) and 4-chloropyridine hydrochloride (7.8 g, 51.8 mmol) in DMF (43 mL) was added potassium tert-butoxide (12.1 g, 108.0 mmol), portionwise. The reaction was heated at 100° C. for 48 h. The mixture was allowed to cool to room temperature and poured into water (400 mL). The resulting solid was removed by filtration and dried under vacuum. Desired compound (6.04 g, 25.3 mmol; 58% yield); 1H NMR (DMSO-d6) δ 8.76 (dd, J=1.7, 4.5, 2H), 8.68 (d, J=2.2, 1H), 8.06-8.13 (m, 2H), 7.92 (d, J=9.2, 1H), 7.75 (dd, J=1.5, 4.6, 2H), 7.07 (dd, J=0.9, 3.5, 1H); ES MS [M+H]+=240. Step 2. Preparation of 1-(4-pyridinyl)-1H-indol-5-amine

Workup

  1. temperatureto cool to room temperature
  2. customThe resulting solid was removed by filtration
  3. customdried under vacuum

Sources & evidence

ORD record
ord-77b2a0d039964e01b937127ea12e1f25
Source dataset
uspto-grants-2005_08
Patent number
US06924290B2

Reaction notes

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