Sodium hydride → 4-(1-Benzyl-3-carbamoylmethyl-2-ethyl-1H-indol-5-yloxy)-butyric acid ethyl ester

HRID 2292795Notes

Reaction equation

HRID 2292795 reaction equation
[CH2:1]([C:3]1[N:4]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:5]2[C:10]([C:11]=1[CH2:12][C:13]([NH2:15])=[O:14])=[CH:9][C:8]([OH:16])=[CH:7][CH:6]=2)[CH3:2].[H-].[Na+].Br[CH2:27][CH2:28][CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31]>>[CH2:33]([O:32][C:30](=[O:31])[CH2:29][CH2:28][CH2:27][O:16][C:8]1[CH:9]=[C:10]2[C:5](=[CH:6][CH:7]=1)[N:4]([CH2:17][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)[C:3]([CH2:1][CH3:2])=[C:11]2[CH2:12][C:13]([NH2:15])=[O:14])[CH3:34]

Participants

4

Reactant 3

HCID 24758Sodium hydrideHCID 76300Ethyl 4-bromobutyrateHCID 105428362-ethyl-5-hydroxy-1-(phenylmethyl)-1H-indole-3-acetamide

Product 1

HCID 105501624-(1-Benzyl-3-carbamoylmethyl-2-ethyl-1H-indol-5-yloxy)-butyric acid ethyl esterYield 55%

Procedure

2-Ethyl-5-hydroxy-1-(phenylmethyl)-1H-indole-3-acetamide (308 mg, 1 mmol) was reacted with 40 mg (1 mmol) of 60% NaH/mineral oil and then with 0.15 mL (1 mmol) of ethyl 4-bromobutyrate as described in Example 56. Part D to give a product that was chromatographed on silica gel eluting with 50% EtOAc/hexane to give 231 mg (55% yield) of [4-[[3-(2-amino-2-oxoethyl)-2-ethyl-1-(phenylmethyl)-1-H-indol-5-yl]oxy]butanoic acid ethyl ester.

Workup

  1. customPart D to give a product that
  2. customwas chromatographed on silica gel eluting with 50% EtOAc/hexane

Sources & evidence

ORD record
ord-e8ba5a7fd10e4ceaa0339daafa731cac
Source dataset
uspto-grants-1997_11
Patent number
US05684034

Reaction notes

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