HCID 59239012, compound → HCID 59239000, compound

HRID 1949123Notes

Reaction equation

HRID 1949123 reaction equation
[CH:1]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:2]=1[C:3]1[CH:4]=[C:5]3[C:26]4[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=4[NH:20][C:6]3=[C:7]([C:14]#[C:15][CH2:16][N:17]([CH3:19])[CH3:18])[C:8]=1[NH:9]2>[Pd].CO>[CH:1]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:2]=1[C:3]1[CH:4]=[C:5]3[C:26]4[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=4[NH:20][C:6]3=[C:7]([CH2:14][CH2:15][CH2:16][N:17]([CH3:19])[CH3:18])[C:8]=1[NH:9]2

Participants

4

Reactant 1

HCID 59239012HCID 59239012, compound

Product 1

HCID 59239000HCID 59239000, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 3-(5,7-dihydroindolo[2,3-b]carbazol-6-yl)-N,N-dimethylprop-2-yn-1-amine (30 mg, 0.08891 mmol), 10% Pd/C (10 mg, 0.0094 mmol) and methanol (20 mL) in a 250-mL hydrogenation bottle was filled with H2 and then degassed via house vacuum. This process was repeated three times. The reaction mixture was shaken at room temperature under H2 (30 psi) for 12 hours. The reaction solution was filtered through celite, and concentrated. The residue was subjected to flash chromatography to provide 3-(5,7-dihydroindolo[2,3-b]carbazol-6-yl)-N,N-dimethylpropan-1-amine. (10.2 mg, 34%). 1H-NMR (400 MHz, DMSO-d6) δ ppm 11.06 (s, 2 H), 8.64 (s, 1 H), 8.12 (d, J=7.6 Hz, 2 H), 7.46 (d, J=8.0 Hz, 2 H), 7.34-7.27 (m, 2 H), 7.17-7.08 (m, 2 H), 3.18 (t, J=7.4 Hz, 2 H), 2.31 (t, J=7.2 Hz, 2 H), 1.96-1.85 (m, 2 H); MS (ESI) m/z 340.3 (M−H)−; MS (ESI) m/z 342.1 (M+H)+

Workup

  1. additionwas filled with H2
  2. customdegassed via house vacuum
  3. filtrationThe reaction solution was filtered through celite
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-6648bea2de664a60834a3e20c8515e77
Source dataset
uspto-grants-2013_03
Patent number
US08399502B2

Reaction notes

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