HCID 10381677, compound → HCID 19040740, compound

HRID 1683920Notes

Reaction equation

HRID 1683920 reaction equation
[CH3:1][N:2]([CH3:24])[CH2:3][CH2:4][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([NH:14][C:15]3[C:20]([N+:21]([O-])=O)=[CH:19][CH:18]=[CH:17][N:16]=3)[CH:12]=2)[NH:7][CH:6]=1>[Pd].C(O)C>[CH3:24][N:2]([CH3:1])[CH2:3][CH2:4][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([NH:14][C:15]3[C:20]([NH2:21])=[CH:19][CH:18]=[CH:17][N:16]=3)[CH:12]=2)[NH:7][CH:6]=1

Participants

4

Reactant 1

HCID 10381677HCID 10381677, compound

Product 1

HCID 19040740HCID 19040740, compoundYield 64.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 3-(2-dimethylaminoethyl)-5-(3-nitropyrid-2-ylamino)-1H-indole (1.27 g, 3.90 mmol), 10% Pd on carbon (200 mg), and absolute ethanol (20 mL) was shaken under a hydrogen atmosphere (3 atm) for 2 hours. The reaction mixture was filtered through diatomaceous earth, and the filtrate was evaporated under reduced pressure. The residue was column chromatographed using silica gel (approximately 40 g) and elution with absolute methanol to afford the title compound (0.74 g, 64%) as an off-white solid: mp., 196.0°-198.0° C. with effervescence; 13C NMR (DMSO-d6) δ145.3, 134.5, 133.6, 132.1, 131.0, 127.3, 122.6, 118.8, 116.1, 114.2, 112.1, 110.8, 108.6, 60.1, 45.2, 23.4; HRMS calculated for C17H21N5 295.1793, found 295.1810. Anal. calcd. for C17H21N5.0.4 C2H6O [ethanol]: C, 68.13; H, 7.52; N, 22.32. Found: C, 68.12; H, 7.19; N, 22.51.

Workup

  1. filtrationThe reaction mixture was filtered through diatomaceous earth
  2. customthe filtrate was evaporated under reduced pressure
  3. customchromatographed
  4. washsilica gel (approximately 40 g) and elution with absolute methanol

Sources & evidence

ORD record
ord-82dccf0912fa435883baa7ca34802958
Source dataset
uspto-grants-1997_06
Patent number
US05639752

Reaction notes

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