Sodium Iodide → 2-{[tert-butyl(dimethyl)silyl]oxy}ethyl-3-(3-iodopropyl)-1H-indole

HRID 590397Notes

Reaction equation

HRID 590397 reaction equation
CS(O[CH2:6][CH2:7][CH2:8][C:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:11]([CH2:18][CH2:19][O:20][Si:21]([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22])[CH:10]=1)(=O)=O.[I-:28].[Na+]>>[Si:21]([O:20][CH2:19][CH2:18][N:11]1[C:12]2[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:9]([CH2:8][CH2:7][CH2:6][I:28])=[CH:10]1)([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22]

Participants

3

Reactant 2

HCID 5238Sodium IodideHCID 1317344763-[1-(2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)-1H-indol-3-yl]propyl methanesulfonate2×

Product 1

HCID 1317344772-{[tert-butyl(dimethyl)silyl]oxy}ethyl-3-(3-iodopropyl)-1H-indoleYield 71.6%

Conditions

Temperature
50 °C

Procedure

To a solution of 3-[1-(2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)-1H-indol-3-yl]propyl methanesulfonate (Intermediate 42; 3.5 g, 8.5 mmol) in ketone (20 mL) was added sodium iodide (2.55 g, 17 mmol). The reaction mixture was stirred overnight at 50° C. The crude reaction was filtered and the solvent was removed under reduced pressure. The crude obtained was purified over silica gel eluting with hexane:ether (100/0 to 0/100) to obtain the title compound (2.7 g, 71%).

Workup

  1. customThe crude reaction
  2. filtrationwas filtered
  3. customthe solvent was removed under reduced pressure
  4. customThe crude obtained
  5. customwas purified over silica gel eluting with hexane

Sources & evidence

ORD record
ord-391a942eadee424c86e996cf716d0b16
Source dataset
uspto-grants-2016_01
Patent number
US09233108B2

Reaction notes

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