HCID 59442033, compound → HCID 59441869, compound

HRID 1014273Notes

Reaction equation

HRID 1014273 reaction equation
[CH2:1]([N:3]([CH2:21][CH3:22])[CH2:4][C:5]([N:7]1[C:15]2[C:10](=[CH:11][C:12]([O:19][CH3:20])=[C:13]([N+:16]([O-])=O)[CH:14]=2)[CH2:9][CH2:8]1)=[O:6])[CH3:2]>CCO.[Pd]>[CH2:1]([N:3]([CH2:4][C:5]([N:7]1[C:15]2[C:10](=[CH:11][C:12]([O:19][CH3:20])=[C:13]([NH2:16])[CH:14]=2)[CH2:9][CH2:8]1)=[O:6])[CH2:21][CH3:22])[CH3:2]

Participants

4

Reactant 1

HCID 59442033HCID 59442033, compound

Product 1

HCID 59441869HCID 59441869, compoundYield 46%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of N,N-diethyl-2-[5-(methyloxy)-6-nitro-2,3-dihydro-1 H-indol-1-yl]-2-oxoethanamine (0.68 g, 2.2 mol) and 10% Pd on carbon (0.06 g) in EtOH (150 mL) was stirred under 1 atm of H2 for 20 h, then filtered through a pad of Celite. The filtrate was concentrated, the residue dissolved in CH2Cl2 and purified by silica gel chromatography using 0-10% MeOH (containing 0.2% NH3)/CH2Cl2to obtain 1-[(diethylamino)acetyl]-5-(methyloxy)-2,3-dihydro-1H-indol-6-amine as a brown solid (281 mg, 46%). 1H NMR (400 MHz, DMSO-d6) δ ppm 0.98 (t, J=7.14 Hz, 6H), 2.57 (q, J=7.02 Hz 4H), 2.97 (t, J=8.24 Hz 2H), 3.28 (s, 2H), 3.71 (s, 3H),4.12 (t, J=8.24 Hz, 2H), 4.62 (s, 2H), 6.70 (s, 1H), 7.54 (s, 1H); ESIMS (M+H)+=278.19.

Workup

  1. filtrationfiltered through a pad of Celite
  2. concentrationThe filtrate was concentrated
  3. dissolutionthe residue dissolved in CH2Cl2
  4. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-e29cf26b159e4d47a54c8e22a450f4ba
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

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