Diisopropylethylamine → 2-[3-((2R)-2-{2-[4-(tert-butyl-dimethylsilyloxy)phenyl]-(2R)-2-(triethylsilyloxy)ethylamino}propyl)-1H-indol-7-yloxy]-N,N-diethylacetamide

HRID 1351925Notes

Reaction equation

HRID 1351925 reaction equation
[Si:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C@@H:15]([O:18][Si:19]([CH2:24][CH3:25])([CH2:22][CH3:23])[CH2:20][CH3:21])[CH2:16]I)=[CH:11][CH:10]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[NH2:26][C@H:27]([CH3:47])[CH2:28][C:29]1[C:37]2[C:32](=[C:33]([O:38][CH2:39][C:40]([N:42]([CH2:45][CH3:46])[CH2:43][CH3:44])=[O:41])[CH:34]=[CH:35][CH:36]=2)[NH:31][CH:30]=1.CCN(C(C)C)C(C)C>O1CCCC1.C(Cl)(Cl)Cl>[NH3:26].[Si:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C@@H:15]([O:18][Si:19]([CH2:24][CH3:25])([CH2:22][CH3:23])[CH2:20][CH3:21])[CH2:16][NH:26][C@H:27]([CH3:47])[CH2:28][C:29]2[C:37]3[C:32](=[C:33]([O:38][CH2:39][C:40]([N:42]([CH2:43][CH3:44])[CH2:45][CH3:46])=[O:41])[CH:34]=[CH:35][CH:36]=3)[NH:31][CH:30]=2)=[CH:11][CH:10]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

7

Reactant 3

HCID 81531DiisopropylethylamineHCID 10968695(R)-2-[3-(2-aminopropyl)-1H-indol-7-yloxy]-N,N-diethyl-acetamideHCID 69457008(R)-1-(tert-Butyldimethylsilyloxy)-4-(2-iodo-1-triethylsilyloxy-ethyl)benzene

Product 2

HCID 222AmmoniaHCID 694597782-[3-((2R)-2-{2-[4-(tert-butyl-dimethylsilyloxy)phenyl]-(2R)-2-(triethylsilyloxy)ethylamino}propyl)-1H-indol-7-yloxy]-N,N-diethylacetamideYield 48.4%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
110 °C

Procedure

(R)-1-(tert-Butyldimethylsilyloxy)-4-(2-iodo-1-triethylsilyloxy-ethyl)benzene (J. Org. Chem., vol. 56, p. 442 (1991)) (65 mg, 0.13 mmol) and (R)-2-[3-(2-aminopropyl)-1H-indol-7-yloxyl]-N,N-diethylacetamide (80 mg, 0.26 mmol) and iPr2NEt (115 μL) are dissolved in tetrahydrofuran (2 mL), and the mixture is stirred at 110° C. for 10 hours. After cooling, the mixture is concentrated and the residue is purified by silica gel column chromatography (chloroform→a saturated ammonia solution in chloroform) to give the desired 2-[3-((2R)-2-{2-[4-(tert-butyl-dimethylsilyloxy)phenyl]-(2R)-2-(triethylsilyloxy)ethylamino}propyl)-1H-indol-7-yloxy]-N,N-diethylacetamide (42 mg, yield: 48%).

Workup

  1. temperatureAfter cooling
  2. concentrationthe mixture is concentrated
  3. customthe residue is purified by silica gel column chromatography (chloroform

Sources & evidence

ORD record
ord-66859058183f4d38b29e1642ac15d846
Source dataset
uspto-grants-2007_05
Patent number
US07217724B2

Reaction notes

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