Potassium Phosphate, Tribasic → 2-[2-(tert-Butyldimethylsilanyloxy)ethyl]-1-[4-(3-pyrrolidin-1-ylpropoxy)phenyl]-1H-indole

HRID 491040Notes

Reaction equation

[Si:1]([O:8][CH2:9][CH2:10][C:11]1[NH:12][C:13]2[C:18]([CH:19]=1)=[CH:17][CH:16]=[CH:15][CH:14]=2)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].I[C:21]1[CH:35]=[CH:34][C:24]([O:25][CH2:26][CH2:27][CH2:28][N:29]2[CH2:33][CH2:32][CH2:31][CH2:30]2)=[CH:23][CH:22]=1.CN(C)CCN.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C1(C)C=CC=CC=1.[Cu]I>[Si:1]([O:8][CH2:9][CH2:10][C:11]1[N:12]([C:21]2[CH:22]=[CH:23][C:24]([O:25][CH2:26][CH2:27][CH2:28][N:29]3[CH2:30][CH2:31][CH2:32][CH2:33]3)=[CH:34][CH:35]=2)[C:13]2[C:18]([CH:19]=1)=[CH:17][CH:16]=[CH:15][CH:14]=2)([C:4]([CH3:6])([CH3:7])[CH3:5])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 100 °C

Procedure

2-[2-(tert-Butyldimethylsilanyloxy)ethyl]-1H-indole (0.11 g, 0.4 mmol) and 1-[3-(4-Iodophenoxy)propyl]pyrrolidine (0.16 g, 0.48 mmol) were dissolved in toluene (0.4 mL), and N,N-dimethylethylenediamine (0.017 mL, 0.16 mmol), copper(I) iodide (30 mg, 0.16 mmol), and potassium phosphate (0.18 g, 0.84 mmol) were added. The reaction was heated at 100° C. overnight. The mixture was filtered through Celite with dichloromethane. The filtrate was concentrated, and taken forward without purification (crude product contains some starting material). LC-MS (C29H42N2O2Si calc'd 478) m/z 479 (M+H).

Workup

filtrationThe mixture was filtered through Celite with dichloromethane
concentrationThe filtrate was concentrated
customtaken forward without purification (crude product

Sources & evidence

ORD record: ord-0b5474bfdca94e8f82c48294e57ce4b4
Source dataset: uspto-grants-2009_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07528262B2

Reaction notes

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