Imidazole → HCID 15174908, compound

HRID 2389355Notes

Reaction equation

HRID 2389355 reaction equation
O[CH2:2][CH2:3][CH2:4][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:7]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH:6]=1.N1C=CN=C1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[I:45]I>CC#N.O>[I:45][CH2:2][CH2:3][CH2:4][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:7]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH:6]=1

Participants

7

Reactant 4

HCID 795ImidazoleHCID 807IodineHCID 11776TriphenylphosphineHCID 68535380HCID 68535380, compound

Product 1

HCID 15174908HCID 15174908, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a stirring solution of tert-butyl 3-(3-hydroxypropyl)-1H-indole-1-carboxylate in MeCN were added imidazole (44 mg), PPh3 (129 mg) and iodine (124 mg) at ambient temperature. After 3 hours, water was added and the mixture was extracted with EtOAc. The organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered and evaporated in vacuo. The residue was purified by silica gel column chromatography (n-hexane:EtOAc=15:1) to give tert-butyl 3-(3-iodopropyl)-1H-indole-1-carboxylate (63 mg).

Workup

  1. extractionthe mixture was extracted with EtOAc
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customThe residue was purified by silica gel column chromatography (n-hexane:EtOAc=15:1)

Sources & evidence

ORD record
ord-4425e3193dfb433c9a3c26dc50ba95bb
Source dataset
uspto-grants-2012_09
Patent number
US08273745B2

Reaction notes

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