Sodium hydride → HCID 86751502, compound

HRID 1069604Notes

Reaction equation

HRID 1069604 reaction equation
[CH:1]1([N:7]2[C:15]3[C:10](=[CH:11][C:12]([OH:16])=[CH:13][CH:14]=3)[C:9]([CH2:17][C:18]([NH2:20])=[O:19])=[C:8]2[CH3:21])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Na+].Br[CH2:25][CH2:26][CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29]>>[CH2:31]([O:30][C:28](=[O:29])[CH2:27][CH2:26][CH2:25][O:16][C:12]1[CH:11]=[C:10]2[C:15](=[CH:14][CH:13]=1)[N:7]([CH:1]1[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1)[C:8]([CH3:21])=[C:9]2[CH2:17][C:18]([NH2:20])=[O:19])[CH3:32]

Participants

4

Reactant 3

HCID 24758Sodium hydrideHCID 76300Ethyl 4-bromobutyrateHCID 21191869HCID 21191869, compound

Product 1

HCID 86751502HCID 86751502, compoundYield 46%

Procedure

1-Cyclohexyl-5-hydroxy-2-methyl-1H-indole-3-acetamide (300 mg, 1.0 mmol) was reacted with 40 mg (1.0 mmol) of 60% NaH/mineral oil and then 0.143 mL (1.0 mmol) of ethyl 4-bromobutyrate as described in Example 50, Part D to give a product that was chromatographed on silica gel (eluted with 2% MeOH/methylene chloride) to give 190 mg (46% yield) of [4-[[3-(2-amino-2-oxoethyl)-1-cyclohexyl-2-methyl-1-H-indol-5-yl]oxy]butanoic acid ethyl ester, mp, 92-94(° C.

Workup

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

Sources & evidence

ORD record
ord-8c21542657a64405975793804415c245
Source dataset
uspto-grants-2001_06
Patent number
US06252084B1

Reaction notes

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