N'-[3-(2-Dimethylamino-ethyl)-1H-indol-5-ylmethylene]-hydrazine-carboxylic acid isobutyl ester → HCID 58882812, compound

HRID 507379Notes

Reaction equation

HRID 507379 reaction equation
[CH2:1]([O:5][C:6]([NH:8][N:9]=[CH:10][C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[NH:16][CH:15]=[C:14]2[CH2:20][CH2:21][N:22]([CH3:24])[CH3:23])=[O:7])[CH:2]([CH3:4])[CH3:3]>[Pd].C(O)C>[CH2:1]([O:5][C:6]([NH:8][NH:9][CH2:10][C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[NH:16][CH:15]=[C:14]2[CH2:20][CH2:21][N:22]([CH3:23])[CH3:24])=[O:7])[CH:2]([CH3:4])[CH3:3]

Participants

4

Reactant 1

HCID 68472493N'-[3-(2-Dimethylamino-ethyl)-1H-indol-5-ylmethylene]-hydrazine-carboxylic acid isobutyl ester

Product 1

HCID 58882812HCID 58882812, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
65 °C

Procedure

A 50 ml pressure vessel is charged with N′-[3-(2-Dimethylamino-ethyl)-1H-indol-5-ylmethylene]-hydrazinecarboxylic acid isobutyl ester (Example 10; 1.76 g, 5.33 mmol), ethanol (25 ml), and the catalyst (5% Pd/C type E-4522, 325 mg). The vessel is sealed, purged with argon (three times and hydrogen (three times), heated in an oil bath to 65° C., and then pressurized with hydrogen (78.4 bar). The stirrer is started (900 rpm), and the hydrogenation allowed to proceed for 21.5 hours. After cooling to ambient temperature the pressure vessel is vented, and the reaction mixture filtered over a pad of Hyflo to remove the catalyst. Removal of the solvent gives the product as a pale yellow residue, which is pure by NMR. 1H-NMR (CD3OD, 300 MHz) δ 0.81 (d, 6H, J=6.8 Hz, CH(CH3)2); 1.78 (m, 1H, CH(CH3)2); 2.27 (s, 6H, N(CH3)2); 2.61, 2.83 (2 m, 2H each, CH2CH2NHMe2); 3.74 (d, 2H, J=6.6 Hz, OCH2); 3.90 (s, 2H, CH2N); 6.95 (s, 1H, H-2); 7.02 (dd, 1H, J=8.3 Hz, J=1.5 Hz, H-6); 7.19 (d, 1H, H-7); 7.43 (s, 1H, H-4). 13C-NMR (CD3OD, 75 MHz) δ 19.70 (CH3); 24.46 (CH2); 29.71 (CHMe2); 45.65 (N(CH3)2); 57.89 (CH2N); 61.64 (CH2NMe2); 72.57 (OCH2); 112.64 (CH); 113.85 (C); 120.42 (CH); 124.06 (CH); 124.33 (CH); 128.89 (C); 129.09 (C); 138.13 (C); 160.03 (C═O).

Workup

  1. customThe vessel is sealed
  2. custompurged with argon (three times and hydrogen (three times)
  3. temperatureAfter cooling to ambient temperature the pressure vessel
  4. filtrationthe reaction mixture filtered over a pad of Hyflo
  5. customto remove the catalyst
  6. customRemoval of the solvent
  7. customgives the product as a pale yellow residue, which

Sources & evidence

ORD record
ord-5fd29b9f01e54a408956b9eb2621efc6
Source dataset
uspto-grants-2010_08
Patent number
US07786156B2

Reaction notes

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