Isopropyl iodide → HCID 69268875, compound

HRID 751513Notes

Reaction equation

HRID 751513 reaction equation
[Si:1]([O:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:14]=[C:15]2[C:19](=[CH:20][CH:21]=1)[NH:18][CH:17]=[CH:16]2)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[CH3:22][C:23](C)([O-])[CH3:24].[K+].IC(C)C>CN(C)C=O.C(OCC)(=O)C>[Si:1]([O:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:14]=[C:15]2[C:19](=[CH:20][CH:21]=1)[N:18]([CH:23]([CH3:24])[CH3:22])[CH:17]=[CH:16]2)([C:4]([CH3:6])([CH3:7])[CH3:5])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 6362Isopropyl iodideHCID 23665647Potassium tert-butoxideHCID 69270516HCID 69270516, compound

Product 1

HCID 69268875HCID 69268875, compoundYield 38%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Dissolve 5-[3-(tert-butyldimethylsilyloxy)propoxy]-1H-indole (1.0 g, 0.327 mmol) in N,N-dimethylformamide (20 mL) under nitrogen. Add 3.6 mL potassium tert-butoxide (1M solution in THF, 1.1 equiv) and stir 10 minutes, then add 2-iodopropane (0.36 mL, 1.1 eq) and stir for 30 minutes. Dilute with ethyl acetate and wash with water then brine. Dry over magnesium sulfate, filter and concentrate. Purification by column chromography (hexanes to 4:1 hexanes:ethyl acetate) affords 0.43 g product (38%) as a clear oil. 1H NMR (400 MHz, DMSO-d6) δ 0.00 (s, 6H), 0.83 (s, 9H), 1.40 (d, J=6.83 Hz, 6H), 1.86 (m, 2H), 3.74 (m, 2H), 3.98 (m, 2H), 4.64 (m, 1H), 6.29 (d, J=2.93 Hz, 1H), 6.71 (m, 1H), 6.99 (d, J=1.95 Hz, 1H), 7.36 (m, 2H).

Workup

  1. washwash with water
  2. dry with materialDry over magnesium sulfate
  3. filtrationfilter
  4. concentrationconcentrate
  5. customPurification by column chromography (hexanes to 4:1 hexanes:ethyl acetate)

Sources & evidence

ORD record
ord-b56eff8e92a24ba9836d670ea9778dd0
Source dataset
uspto-grants-2008_07
Patent number
US07405305B2

Reaction notes

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