Water → HCID 22324310, compound

HRID 496014Notes

Reaction equation

HRID 496014 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, 1 H), 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-783c0963aead4f8d81fa659e06a28cd4
Source dataset
uspto-grants-2005_09
Patent number
US06943172B2

Reaction notes

Loading…