Water → HCID 18926510, compound

HRID 1600181Notes

Reaction equation

HRID 1600181 reaction equation
CC(C)([O-])C.[K+].[F:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][C:15]2[C:23]3[C:18](=[CH:19][CH:20]=[C:21]([N+:24]([O-:26])=[O:25])[CH:22]=3)[NH:17][CH:16]=2)=[CH:10][CH:9]=1.[C:27]([O:31][CH3:32])(=[O:30])[CH:28]=[CH2:29].O>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O1CCOCC1.CCOCC>[F:7][C:8]1[CH:9]=[CH:10][C:11]([CH2:14][C:15]2[C:23]3[C:18](=[CH:19][CH:20]=[C:21]([N+:24]([O-:26])=[O:25])[CH:22]=3)[N:17]([CH2:29][CH2:28][C:27]([O:31][CH3:32])=[O:30])[CH:16]=2)=[CH:12][CH:13]=1

Participants

8

Reactant 4

HCID 962WaterHCID 7294Methyl Acrylate2×HCID 18926546HCID 18926546, compoundHCID 23665647Potassium tert-butoxide2×

Product 1

HCID 18926510HCID 18926510, compoundYield 65.5%

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalyst2×HCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent

Procedure

Tetrabutylammonium bromide (0.262 g) and potassium t-butoxide (100 mg) wereadded to a stirred solution of 3-(4-fluorophenylmethyl)-5-nitro-1H-indole (2.20 g) and methyl acrylate (0.84 g) in dioxan (30 ml) and the solution was stirred at room temperature for 66 hours. Further quantities of methylacrylate (0.5 g), tetrabutylammonium bromide (262 mg) and potassium t-butoxide (100 mg) were added and stirring was continued for an additional 5 hours. The solution was poured into water and the mixture wasextracted twice with ether. The combined ether extracts were washed with water, dried (Na2SO4) and evaporated. The residue was chromatographed on silica gel using hexane/dichloromethane (1:4) as eluent. The product fractions were combined and evaporated to give the title compound as a gum (1.90 g). Found: C,64.43; H,4.39; N,7.65. C19H17FN2O4 requires: C,64.03; H,4.81; N,7.86%.

Workup

  1. stirringstirring
  2. waitwas continued for an additional 5 hours
  3. washThe combined ether extracts were washed with water
  4. dry with materialdried (Na2SO4)
  5. customevaporated
  6. customThe residue was chromatographed on silica gel
  7. customevaporated

Sources & evidence

ORD record
ord-3efc5389b06444c8af578d1478356be4
Source dataset
uspto-grants-1998_04
Patent number
US05744488

Reaction notes

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