Isopropyl iodide → HCID 67073393, compound

HRID 901097Notes

Reaction equation

HRID 901097 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([O:15][C@H:16]1[CH2:20][CH2:19][N:18]([CH2:21][C:22]3C=CC=CC=3)[CH2:17]1)=[CH:10][CH:9]=2)=[O:5])[CH3:2].[C:28]([O-])([O-])=O.[K+].[K+].IC(C)C>[Pd].C(O)(=O)C>[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([O:15][C@H:16]1[CH2:20][CH2:19][N:18]([CH:21]([CH3:22])[CH3:28])[CH2:17]1)=[CH:10][CH:9]=2)=[O:5])[CH3:2]

Participants

6

Reactant 3

HCID 6362Isopropyl iodideHCID 11430Potassium CarbonateHCID 67073446HCID 67073446, compound

Product 1

HCID 67073393HCID 67073393, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 18 g (49 mmol) 5-((S)-1-benzyl-pyrrolidin-3-yloxy)-1H-indole-2-carboxylic acid ethyl ester, 28.3 ml acetic acid and 2 g Pd/C 10% was hydrogenated with H2 at room temperature during 16 h. The mixture was filtered and the filtrate evaporated to dryness. The residue was taken up in 500 ml DMF and 34.1 g (247 mmol) K2CO3 and 42 g (247 mmol) 2-iodopropane was added and the mixture was stirred for 4 h at 50° C. After filtration and evaporation the residue was purified on silica eluting with a gradient formed from DCM/MeOH (2N NH3) 98/2 to 92/8 to yield after evaporation of the product fractions 60% of the title compound as light brown solid. MS (m/e): 317.3 (MH+, 100%).

Workup

  1. filtrationThe mixture was filtered
  2. customthe filtrate evaporated to dryness
  3. filtrationAfter filtration and evaporation the residue
  4. customwas purified on silica eluting with a gradient
  5. customformed from DCM/MeOH (2N NH3) 98/2 to 92/8
  6. customto yield
  7. customafter evaporation of the product fractions 60% of the title compound as light brown solid

Sources & evidence

ORD record
ord-bc21011539f940acba0c502a9845af12
Source dataset
uspto-grants-2008_04
Patent number
US07361682B2

Reaction notes

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