HCID 68472205, compound → HCID 58882797, compound

HRID 507380Notes

Reaction equation

HRID 507380 reaction equation
[C: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])([CH3:4])([CH3:3])[CH3:2]>[Pd].C(O)C>[C: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]([CH3:24])[CH3:23])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 68472205HCID 68472205, compound

Product 1

HCID 58882797HCID 58882797, compoundYield 90.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
87 °C

Procedure

A 50 ml pressure vessel is charged with N′-[3-(2-Dimethylamino-ethyl)-1H-indol-5-ylmethylene]-hydrazinecarboxylic acid tert-butyl ester (Example 11; 1.20 g, 3.63 mmol), ethanol (18 ml), and the catalyst (5% Pd/C type E-4522, 240 mg). The vessel is sealed, purged with argon (three times and hydrogen (three times), heated in an oil bath to 87° C., and then pressurized with hydrogen (43.4 bar). The stirrer is started (900 rpm), and the hydrogenation allowed to proceed for 18 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 (1.092 g, 90.4%) as a pale yellow residue, which is pure by NMR. 1H-NMR (CD3OD, 300 MHz) δ 1.33 (s, 9H, C(CH3)3); 2.45 (s, 6H, N(CH3)2); 2.84-2.96 (m, 4H, CH2CH2NMe2); 3.88 (s, 2H, CH2N); 7.00 (br s, 1H, H-2); 7.02 (dd, 1H, J=8.3 Hz, J=1.5 Hz, H-6); 7.21 (d, 1H, H-7); 7.45 (s, 1H, H-4). 13C-NMR (CD3OD, 75 MHz) δ 23.69 (CH2); 29.11 (C(CH3)3); 45.03 (N(CH3)2); 57.94 (CH2N); 60.66 (CH2NMe2); 112.41 (C); 112.74 (CH); 120.30 (CH); 124.53 (CH); 128.89 (C); 129.15 (C); 138.17 (C); 162.32 (br, 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

Sources & evidence

ORD record
ord-b6f56de009f54004a8f1970f3e7112d7
Source dataset
uspto-grants-2010_08
Patent number
US07786156B2

Reaction notes

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