HCID 69234246, compound → HCID 69235087, compound

HRID 40645Notes

Reaction equation

HRID 40645 reaction equation
[CH3:1][C:2]1[NH:3][C:4]2[C:9]([CH:10]=1)=[C:8]([O:11][CH2:12][CH:13]([OH:35])[CH2:14][N:15]1[CH2:22][CH:21]3[N:23]([C:25]4[CH:34]=[CH:33][C:32]5[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=5)[CH:26]=4)[CH2:24][CH:16]1[CH2:17][CH:18]=[CH:19][CH2:20]3)[CH:7]=[CH:6][CH:5]=2>[Pd].CO>[CH3:1][C:2]1[NH:3][C:4]2[C:9]([CH:10]=1)=[C:8]([O:11][CH2:12][CH:13]([OH:35])[CH2:14][N:15]1[CH2:22][CH:21]3[N:23]([CH:25]4[CH2:34][CH2:33][C:32]5[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=5)[CH2:26]4)[CH2:24][CH:16]1[CH2:17][CH2:18][CH2:19][CH2:20]3)[CH:7]=[CH:6][CH:5]=2

Participants

4

Reactant 1

HCID 69234246HCID 69234246, compound

Product 1

HCID 69235087HCID 69235087, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

1-(2-Methyl-1H-indol-4-yloxy)-3-(9-naphthalen-2-yl-7,9-diaza-bicyclo[4.2.2]dec-3-en-7-yl)-propan-2-ol (0.05 g, 0.107 mmol), 10% Pd/C (0.05 g), methanol (15 mL) were placed in an hydrogenation bottle under H2 atmosphere (60 psi) and shaken overnight. The resulting mixture was filtered and the solvent evaporated under reduced pressure to yield a crude solid. The crude solid was purified with flash chromatography [20% Ethyl acetate/heptane] to yield the title compound as a residue.

Workup

  1. filtrationThe resulting mixture was filtered
  2. customthe solvent evaporated under reduced pressure
  3. customto yield a crude solid
  4. customThe crude solid was purified with flash chromatography [20% Ethyl acetate/heptane]

Sources & evidence

ORD record
ord-3d47d109c1684c92860da6f335f73dd9
Source dataset
uspto-grants-2013_09
Patent number
US08530475B2

Reaction notes

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