Indole-5-carboxaldehyde → HCID 178517955, compound

HRID 1967132Notes

Reaction equation

HRID 1967132 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][C:8]([NH2:10])=[CH:9][C:4]=2[N:3]=[CH:2]1.[NH:11]1[C:19]2[C:14](=[CH:15][C:16]([CH:20]=O)=[CH:17][CH:18]=2)[CH:13]=[CH:12]1.[O:22]([C:24]#[N:25])[K].Cl.N1C=CC=CC=1.[N+:33]([CH:35]1[CH2:39][CH2:38][CH2:37][CH2:36]1)#[C-:34]>CO>[NH:1]1[C:5]2[CH:6]=[CH:7][C:8]([N:10]3[CH:20]([C:16]4[CH:15]=[C:14]5[C:19](=[CH:18][CH:17]=4)[NH:11][CH:12]=[CH:13]5)[C:34](=[N:33][CH:35]4[CH2:39][CH2:38][CH2:37][CH2:36]4)[NH:25][C:24]3=[O:22])=[CH:9][C:4]=2[N:3]=[CH:2]1

Participants

7

Reactant 5

HCID 589040Indole-5-carboxaldehydeHCID 2734784Cyclopentyl IsocyanideHCID 10176127Pyridinium chlorideHCID 178418250HCID 178418250, compoundHCID 178507353HCID 178507353, compound

Product 1

HCID 178517955HCID 178517955, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

1H-Benzoimidazol-5-ylamine (1 mmol) and 1H-Indole-5-carbaldehyde (1 mmol) were combined in methanol (2 ml, dry). After 2 hours 2 ml of a solution of KOCN (KSCN) (2 mmol) and Pyridinehydrochloride (2 mmol) in MeOH is added was added. Finally Isocyano-cyclopentane (1 mmol) is added. The reaction was stirred at room temperature for 48 h. After evaporation of the solvent the residue was purified with chromatographic methods. Yield: 0.107 g (27%); mp: 210° C., 1H-NMR (400 MHz, DMSO-D6): 1.20-1.25 (m, 1H, CH2), 1.38-1.56 (m, 5H, CH2), 1.70-1.79 (m, 1H, CH2), 1.82-1.90 (m, 1H, CH2), 4.08-4.14 (m, 1H, CH2—CH), 5.91 (s, 1H, CH—N), 6.33-6.36 (m, 1H, Ar), 6.85 (dd, 3J=8.3 Hz, 4J=1.7 Hz, 1H, Ar), 7.24-7.33 (m, 4H, 3H Ar, 1H Benzimid), 7.52 (s, 1H, Benzimid), 7.63 (s, 1H, Benzimid), 7.86 (m, 1H, NH), 8.06 (s, 1H, Benzimid), 11.05 (s, 1H, NH), MS m/z 399.4 (M+H)+, HPLC (254 nm): rt 2.56 min (100%), calc: C, 69.33; H, 5.57; N, 21.09. found.: C, 63.34; H, 6.16; N, 19.04 corresponds to C23H22N6O+2.0H2O

Workup

  1. additionwas added
  2. customAfter evaporation of the solvent the residue
  3. customwas purified with chromatographic methods
  4. customrt 2.56 min (100%)

Sources & evidence

ORD record
ord-0e125cdb4b3840bb9c47b17897c49601
Source dataset
uspto-grants-2013_04
Patent number
US08420684B2

Reaction notes

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