Sodium hydride → HCID 10647569, compound

HRID 1069602Notes

Reaction equation

HRID 1069602 reaction equation
[CH2:1]([N:11]1[C:19]2[C:14](=[CH:15][C:16]([OH:20])=[CH:17][CH:18]=2)[C:13]([CH2:21][C:22]([NH2:24])=[O:23])=[C:12]1[CH3:25])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].[H-].[Na+].Br[CH2:29][CH2:30][CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33]>>[CH2:35]([O:34][C:32](=[O:33])[CH2:31][CH2:30][CH2:29][O:20][C:16]1[CH:15]=[C:14]2[C:19](=[CH:18][CH:17]=1)[N:11]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10])[C:12]([CH3:25])=[C:13]2[CH2:21][C:22]([NH2:24])=[O:23])[CH3:36]

Participants

4

Reactant 3

HCID 24758Sodium hydrideHCID 76300Ethyl 4-bromobutyrateHCID 10736258HCID 10736258, compound

Product 1

HCID 10647569HCID 10647569, compoundYield 55%

Procedure

[4-[[3-(2-Amino-2-oxoethyl)-1-decyl-2-methyl-1-H-indol-5-yl]oxy]butanois acid ethyl ester. 1-Decyl-5-hydroxy-2-methyl-1H-indole-3-acetamide (310 mg, 3.35 mmol) was reacted with 96 mg (2.4 mmol) of 50% NaH/mineral oil and then 0.32 mL (2.4 mmol) of ethyl 4-bromobutyrate as described in Example 50, Part D to give a product that was chromatographed on silica gel (eluted with 3% MeOH/methylene chloride) to give 590 mg (55% yield) of [4-[[3-(2-amino-2-oxoethyl)-1-decyl-2-methyl-1-H-indol-5-yl]oxy]butanoic acid ethyl ester, mp, 93-95° C.

Workup

  1. customto give a product that
  2. customwas chromatographed on silica gel (eluted with 3% MeOH/methylene chloride)

Sources & evidence

ORD record
ord-6319d213232d4bdbbe2861e75c3bbdc7
Source dataset
uspto-grants-2001_06
Patent number
US06252084B1

Reaction notes

Loading…