Ethyl bromoacetate → tert-Butyl[1-(2-ethoxy-2-oxoethyl)-3-nitro-1H-indol-4-yl]acetate

HRID 2426200Notes

Reaction equation

HRID 2426200 reaction equation
[C:1]([O:5][C:6](=[O:20])[CH2:7][C:8]1[CH:16]=[CH:15][CH:14]=[C:13]2[C:9]=1[C:10]([N+:17]([O-:19])=[O:18])=[CH:11][NH:12]2)([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].Br[CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26]>CN(C=O)C>[C:1]([O:5][C:6](=[O:20])[CH2:7][C:8]1[CH:16]=[CH:15][CH:14]=[C:13]2[C:9]=1[C:10]([N+:17]([O-:19])=[O:18])=[CH:11][N:12]2[CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 57426200tert-Butyl [3-nitro-1H-indol-4-yl]acetate

Product 1

HCID 57426201tert-Butyl[1-(2-ethoxy-2-oxoethyl)-3-nitro-1H-indol-4-yl]acetate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of tert-butyl[3-nitro-1H-indol-4-yl]acetate from Step D (385 mg, 1.39 mmol) in DMF (5 mL) at ambient temperature was added sodium hydride (60 mg of a 60% dispersion in mineral oil, 1.50 mmol). The reaction mixture was stirred for 5 min, then ethyl bromoacetate (256 mg, 1.53 mmol) was added and stirring was continued for 10 min. The reaction was quenched with saturated aqueous NaHCO3 (5 mL) and extracted with CHCl3 (2×25 mL). The combined organic extracts were dried over Na2SO4, filtered, and concentrated in vacuo. The crude product was purified by silica gel chromatography, eluting with a gradient of hexane:EtOAc—90:10 to 40:60, to give the title compound. MS: m/z=307 (M—C4H7).

Workup

  1. stirringstirring
  2. waitwas continued for 10 min
  3. customThe reaction was quenched with saturated aqueous NaHCO3 (5 mL)
  4. extractionextracted with CHCl3 (2×25 mL)
  5. dry with materialThe combined organic extracts were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude product was purified by silica gel chromatography
  9. washeluting with a gradient of hexane

Sources & evidence

ORD record
ord-b8107d38db924458a30d0c7414adbda5
Source dataset
uspto-grants-2011_06
Patent number
US07968540B2

Reaction notes

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