3-Pyridinepropanol → 3-(3-Pyridyl)propyl 9-(2,5-dichlorobenzyl)-9H-beta-carboline-3-carboxylate

HRID 992569Notes

Reaction equation

HRID 992569 reaction equation
N1([C:6]([C:8]2[N:9]=[CH:10][C:11]3[N:12]([CH2:21][C:22]4[CH:27]=[C:26]([Cl:28])[CH:25]=[CH:24][C:23]=4[Cl:29])[C:13]4[C:18]([C:19]=3[CH:20]=2)=[CH:17][CH:16]=[CH:15][CH:14]=4)=[O:7])C=CN=C1.[N:30]1[CH:35]=[CH:34][CH:33]=[C:32]([CH2:36][CH2:37][CH2:38][OH:39])[CH:31]=1>C1(C)C=CC=CC=1>[Cl:29][C:23]1[CH:24]=[CH:25][C:26]([Cl:28])=[CH:27][C:22]=1[CH2:21][N:12]1[C:11]2[CH:10]=[N:9][C:8]([C:6]([O:39][CH2:38][CH2:37][CH2:36][C:32]3[CH:31]=[N:30][CH:35]=[CH:34][CH:33]=3)=[O:7])=[CH:20][C:19]=2[C:18]2[C:13]1=[CH:14][CH:15]=[CH:16][CH:17]=2

Participants

4

Reactant 2

HCID 178613-PyridinepropanolHCID 99319523-(1-imidazolylcarbonyl)-9-(2,5-dichlorobenzyl)-9H-beta-carboline

Product 1

HCID 98484103-(3-Pyridyl)propyl 9-(2,5-dichlorobenzyl)-9H-beta-carboline-3-carboxylateYield 80%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A suspension of 3-(1-imidazolylcarbonyl)-9-(2,5-dichlorobenzyl)-9H-β-carboline (505 mg, 1.20 mmol) and 3-pyridinepropanol (8.2 g, 60 mmol) was heated at 80° C. in toluene (15 mL) for 22 hours. The resulting solution was cooled to room temperature, and extracted several times with water before drying the organic phase with Na2SO4. Evaporation of the solvent followed by preparative thin layer chromatography of the resulting crude material with hexane/ethyl acetate (6:4) as eluent furnished the desired product (470 mg, 80% yield) as a pale yellow solid. 1H NMR (CDCl3) δ8.91 (s, 1H), 8.88 (s, 1H), 8.56 (s, 1H), 8.48 (s, 1H), 8.31 (d,J=8.0 Hz, 1H), 7.67 (AB q, J=7.4 Hz, 1H), 7.60 (d, J=7.8 Hz, 1H), 7.42-7.48 (m, 3H), 7.22-7.28 (m, 2H), 6.60 (s, 1H), 5.70 (s, 2H), 4.53 (t,J=6.5 Hz, 3H), 2.87 (t, J=7.7 Hz, 3H), 2.26 (t, J=7.3 Hz, 3H); MS (ACPl; (M+H)+) m/z 490.

Workup

  1. extractionextracted several times with water
  2. dry with materialbefore drying the organic phase with Na2SO4
  3. customEvaporation of the solvent

Sources & evidence

ORD record
ord-5baa9bc6f7b24ee3ac60c7d5f7eb8b38
Source dataset
uspto-grants-2002_10
Patent number
US06469021B1

Reaction notes

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