Sodium hydride → HCID 10521936, compound

HRID 2292809Notes

Reaction equation

HRID 2292809 reaction equation
[CH3:1][O:2][C:3](=[O:28])[CH2:4][O:5][C:6]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:7]=1[C:8]([CH2:24][C:25]([NH2:27])=[O:26])=[C:9](CC)[N:10]2[CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(C1N(CC2C=CC=CC=2)C2C(C=1CC(N)=O)=C(O)C=CC=2)C.[H-].[Na+].BrCC(OC)=O>CN(C=O)C.O>[CH3:1][O:2][C:3](=[O:28])[CH2:4][O:5][C:6]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:7]=1[C:8]([CH2:24][C:25]([NH2:27])=[O:26])=[CH:9][N:10]2[CH2:15][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 60984Methyl bromoacetateHCID 10804743HCID 10804743, compoundHCID 10833640HCID 10833640, compound

Product 1

HCID 10521936HCID 10521936, compoundYield 34%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

2-[[3-(2-Amino-2-oxoethyl)-2-ethyl-1-(phenylmethyl)-1H-indol-4-yl]oxy]acetic acid methyl ester. 2-Ethyl-4-hydroxy-1-(phenylmethyl)-1H-indole-3-acetamide (135 mg, 0.44 mmol) was added to 17.6 mg (0.44 mmol) of NaH/mineral oil (washed with hexanes) in 5 mL of DMF, stirred 1.5 hours, 0.04 mL (0.44 mmol) of methyl 2-bromoacetate added and stirring maintained for 3 hours. The mixture was diluted with water, extracted with ethyl acetate. The ethyl acetate was washed with brine, dried (MgSO4) and concentrated. The residue was chromatographed on silica gel eluting with 2% MeOH/ethyl acetate to give 34 mg (34% yield) of 2-[[3-(2-amino-2-oxoethyl)-1-(phenylmethyl)-1H-indol-4-yl]oxy]acetic acid methyl ester.

Workup

  1. stirringstirring
  2. temperaturemaintained for 3 hours
  3. extractionextracted with ethyl acetate
  4. washThe ethyl acetate was washed with brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. customThe residue was chromatographed on silica gel eluting with 2% MeOH/ethyl acetate

Sources & evidence

ORD record
ord-dbc3b2094e384239b4a70a6c87994c10
Source dataset
uspto-grants-1997_11
Patent number
US05684034

Reaction notes

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