HCID 59238895, compound → HCID 59239005, compound

HRID 1949107Notes

Reaction equation

HRID 1949107 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10]1[C:9]([O:15][CH2:16][CH2:17][N:18]([CH2:21][CH3:22])[CH2:19][CH3:20])=[C:8]3[NH:23][C:24]4[CH:25]=[CH:26][C:27](Br)=[CH:28][C:29]=4[C:7]3=[CH:6][C:5]2=1>CN(C=O)C.[Pd]>[CH:3]1[CH:2]=[CH:14][CH:13]=[C:12]2[C:4]=1[C:5]1[CH:6]=[C:7]3[C:29]4[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=4[NH:23][C:8]3=[C:9]([O:15][CH2:16][CH2:17][N:18]([CH2:19][CH3:20])[CH2:21][CH3:22])[C:10]=1[NH:11]2

Participants

4

Reactant 1

HCID 59238895HCID 59238895, compound

Product 1

HCID 59239005HCID 59239005, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-(2,10-dibromo-5,7-dihydroindolo[2,3-b]carbazol-6-yloxy)-N,N-diethylethanamine (133.0 mg, 0.2513 mmol) and 10% Pd/C (0.05 equivalent) in DMF (8 mL) in a hydrogenation flask was filled with H2 and then evacuated with house vacuum for three times, and then filled with H2 (30˜40 psi). The reaction was stirred at room temperature overnight. When TLC and MS showed the reaction was complete, the DMF solvent was removed under vacuum pump. The residue was dissolved in methanol and filtered through celite. The crude product was purified by flash chromatography to provide the desired product 2-(5,7-dihydroindolo[2,3-b]carbazol-6-yloxy)-N,N-diethylethanamine (59.3 mg, 64%). 1H-NMR (400 MHz, CD3OD) δ ppm 8.47 (s, 1 H), 8.09 (d, J=7.6 Hz, 2 H), 7.49 (d, J=8.0 Hz, 2 H), 7.33 (t, J=8.0 Hz, 2 H), 7.16 (t, J=7.6 Hz, 2 H), 4.57 (t, J=5.0 Hz, 2 H), 3.79 (t, J=5.0 Hz, 2 H), 3.49 (q, J=7.6 Hz, 4 H), 1.45 (t, J=7.6 Hz, 6 H); MS (ESI) m/z 370.3 (M−H)−; MS (ESI) m/z 372.1 (M+H)+

Workup

  1. additionwas filled with H2
  2. customevacuated with house vacuum for three times
  3. additionfilled with H2 (30˜40 psi)
  4. customthe DMF solvent was removed under vacuum pump
  5. dissolutionThe residue was dissolved in methanol
  6. filtrationfiltered through celite
  7. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-88d9a03f4e934818b54d741c73319e0c
Source dataset
uspto-grants-2013_03
Patent number
US08399502B2

Reaction notes

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