Ethyl bromoacetate → HCID 66636183, compound

HRID 1094146Notes

Reaction equation

HRID 1094146 reaction equation
[H-].[Na+].[CH:3]([C:6]1[NH:7][C:8]2[C:13]([C:14]=1[CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])=[C:12]([N+:21]([O-:23])=[O:22])[CH:11]=[CH:10][CH:9]=2)([CH3:5])[CH3:4].Br[CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27]>CN(C=O)C>[CH:3]([C:6]1[N:7]([CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])[C:8]2[C:13]([C:14]=1[CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])=[C:12]([N+:21]([O-:23])=[O:22])[CH:11]=[CH:10][CH:9]=2)([CH3:4])[CH3:5]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 57426223HCID 57426223, compound

Product 1

HCID 66636183HCID 66636183, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (45 mg of a 60% dispersion in mineral oil, 1.13 mmol) was added to a solution of ethyl (2-isopropyl-4-nitro-1H-indol-3-yl)acetate from Step E (300 mg, 1.03 mmol) in DMF (10 mL). After 5 min, ethyl bromoacetate (0.126 mL, 1.13 mmol) was added dropwise and the reaction mixture was stirred at ambient temperature for 30 min. The reaction mixture was quenched with saturated aqueous NaHCO3 (10 mL) and extracted with CHCl3 (3×25 mL). The combined organic extracts were washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo. The crude product was purified by silica gel chromatography, eluting with a gradient of CHCl3:MeOH—100:0 to 95:5, to give the title compound. MS: m/z=377 (M+1).

Workup

  1. customThe reaction mixture was quenched with saturated aqueous NaHCO3 (10 mL)
  2. extractionextracted with CHCl3 (3×25 mL)
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by silica gel chromatography
  8. washeluting with a gradient of CHCl3

Sources & evidence

ORD record
ord-0f236bbc85a64cbfb4ba59743938ffea
Source dataset
uspto-grants-2012_03
Patent number
US08133891B2

Reaction notes

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