Sodium hydride → HCID 10761402, compound

HRID 2292787Notes

Reaction equation

HRID 2292787 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4]([CH2:19][C:20]([NH2:22])=[O:21])=[C:5]([CH3:18])[N:6]2[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[H-].[Na+].Br[CH2:26][C:27]([O:29][CH3:30])=[O:28]>>[CH3:30][O:29][C:27](=[O:28])[CH2:26][O:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4]([CH2:19][C:20]([NH2:22])=[O:21])=[C:5]([CH3:18])[N:6]2[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 3

HCID 24758Sodium hydrideHCID 60984Methyl bromoacetateHCID 10541824HCID 10541824, compound

Product 1

HCID 10761402HCID 10761402, compoundYield 76%

Procedure

Using the procedure in Example 37 294 mg (1 mmol) of 4-hydroxy-2-methyl-1-(phenylmethyl)-1H-indole-3-acetamide was treated with 40 mg (1 mmol) of 60% NaH/mineral oil and 0.10 mL (1 mmol) of methyl 2-bromoacetate to give, after silica chromatography (eluted with 50% EtOAc/hexane, then EtOAc, followed by 2% MeOH/EtOAc), 278 mg (76% yield) of 2-[[3-(2-amino-2-oxoethyl)-2-methyl-1-(phenylmethyl)-1H-indol-4-yl]oxy]acetic acid methyl ester, mp, 206°-208° C.

Workup

  1. customto give
  2. washafter silica chromatography (eluted with 50% EtOAc/hexane

Sources & evidence

ORD record
ord-14d99cdd85874e3da764fef0e248f5d2
Source dataset
uspto-grants-1997_11
Patent number
US05684034

Reaction notes

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