Water → Methyl 3-[4-({[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-[2-(1H-indol-3-yl)-ethyl]-amino}-methyl)-phenyl]-acrylate

HRID 416208Notes

Reaction equation

HRID 416208 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][CH2:11][NH:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([CH:20]=[CH:21][C:22]([O:24][CH3:25])=[O:23])=[CH:16][CH:15]=2)=[CH:2]1.C(N(C(C)C)CC)(C)C.Br[CH2:36][CH2:37][O:38][Si:39]([C:42]([CH3:45])([CH3:44])[CH3:43])([CH3:41])[CH3:40].O>CS(C)=O>[C:42]([Si:39]([CH3:41])([CH3:40])[O:38][CH2:37][CH2:36][N:12]([CH2:13][C:14]1[CH:15]=[CH:16][C:17]([CH:20]=[CH:21][C:22]([O:24][CH3:25])=[O:23])=[CH:18][CH:19]=1)[CH2:11][CH2:10][C:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[NH:1][CH:2]=1)([CH3:45])([CH3:44])[CH3:43]

Participants

6

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 3608067(2-Bromoethoxy)-tert-butyldimethylsilaneHCID 59036879Methyl 3-(4-{[2-(1H-indol-3-yl)-ethylamino]-methyl}-phenyl)-acrylate

Product 1

HCID 59036876Methyl 3-[4-({[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-[2-(1H-indol-3-yl)-ethyl]-amino}-methyl)-phenyl]-acrylateYield 97.6%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
52.5 °C

Procedure

To a stirred solution of 2 (2.82 g, 8.44 mmol) and diisopropylethylamine (2.21 mL, 12.66 mmol) in anhydrous DMSO (22 mL) at room temperature under nitrogen was added (2-bromo-ethoxy)-tert-butyl-dimethylsilane (2.17 mL, 10.12 mmol). The reaction mixture was heated at 50-55° C. for 24 h, poured into water and extracted with CH2Cl2. The organic layer was dried over MgSO4, filtered, and concentrated. The crude product was purified by flash chromatography on silica gel (AcOEt/CH2Cl2, 15/85, plus a few drops of NH4OH) to afford the title compound 3 (4.06 g, 8.24 mmol, 97% yield) as a dark orange oil.

Workup

  1. extractionextracted with CH2Cl2
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude product was purified by flash chromatography on silica gel (AcOEt/CH2Cl2, 15/85, plus a few drops of NH4OH)

Sources & evidence

ORD record
ord-1890850da9a748f18d63f8d7eb234db6
Source dataset
uspto-grants-2012_01
Patent number
US08088805B2

Reaction notes

Loading…