Acetic Acid → HCID 118666149, compound

HRID 630478Notes

Reaction equation

HRID 630478 reaction equation
[N:1]1([C:7]([C:9]2[CH:17]=[C:16]3[C:12]([C:13]([C:18](=O)[CH3:19])=[CH:14][NH:15]3)=[CH:11][CH:10]=2)=[O:8])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.C(O)(=O)C>C(O)C.[Pd]>[CH2:18]([C:13]1[C:12]2[C:16](=[CH:17][C:9]([C:7]([N:1]3[CH2:2][CH2:3][O:4][CH2:5][CH2:6]3)=[O:8])=[CH:10][CH:11]=2)[NH:15][CH:14]=1)[CH3:19]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 118666355HCID 118666355, compound

Product 1

HCID 118666149HCID 118666149, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

1-(6-(Morpholine-4-carbonyl)-1H-indol-3-yl)ethanone (730 mg, 2.68 mmol) in acetic acid (1.53 ml, 26.8 mmol) and ethanol (50 ml) was hydrogenated in the presence of 10% Pd/C (285 mg, 0.27 mmol) for 72 h at room temperature, and then for 3 h at 50° C. After cooling to room temperature, the suspension was filtered over Celite and washed with ethanol. The solvent was evaporated and the residue repeatedly co-distilled with toluene and dichloromethane. White solid. Yield: 228 mg (33% of theory). HPLC-MS: m/z [M+H]+=259

Workup

  1. filtrationthe suspension was filtered over Celite
  2. washwashed with ethanol
  3. customThe solvent was evaporated

Sources & evidence

ORD record
ord-f21a1c8280794ac3a497c84e7855164b
Source dataset
uspto-grants-2016_04
Patent number
US09315490B2

Reaction notes

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