Sodium hydride → HCID 18926596, compound

HRID 1600179Notes

Reaction equation

HRID 1600179 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[C:7]2[C:13]1[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=1)([O-:3])=[O:2].[H-].[Na+].Br[CH2:22][CH2:23][CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26]>CN(C)C=O>[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]([CH2:22][CH2:23][CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH:8]=[C:7]2[C:13]1[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 24758Sodium hydride2×HCID 76300Ethyl 4-bromobutyrate2×HCID 18926547HCID 18926547, compound

Product 1

HCID 18926596HCID 18926596, compoundYield 70.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-Nitro-3-(3-pyridyl)-1H-indole (0.60 g) was added portionwise to a stirredsuspension of sodium hydride (0.11 g of 60% dispersion in mineral oil) in dry N,N-dimethylformamide (10 ml) at room temperature, and the mixture wasstirred for 30 minutes. Ethyl 4-bromobutanoate (0.40 g) was added and the mixture was stirred for 18 hours. Further sodium hydride (0.11 g of 60% dispersion) was added, the mixture was stirred for 30 minutes and then further ethyl 4-bromobutanoate (0.40 g) was added. Stirring was continued for an additional 4 hours and then the mixture was partitioned between ethyl acetate and water. The organic layer was separated, washed twice with water and dried (MgSO4). The solvent was evaporated and the residue was chromatographed using dichloromethane/methanol (100:1) as eluent. The product fractions were combined and evaporated, and the residue was triturated with ether to give the title compound (0.51 g), m.p. 76°-78° C. Found: C,64.92; H,5.48; N,11.95. C19 H19N3O4 requires: C,64.58; H,5.42; N,11.89%.

Workup

  1. stirringthe mixture was stirred for 30 minutes
  2. stirringStirring
  3. waitwas continued for an additional 4 hours
  4. customthe mixture was partitioned between ethyl acetate and water
  5. customThe organic layer was separated
  6. washwashed twice with water
  7. dry with materialdried (MgSO4)
  8. customThe solvent was evaporated
  9. customthe residue was chromatographed
  10. customevaporated
  11. customthe residue was triturated with ether

Sources & evidence

ORD record
ord-870492e014ab48cfb263813444913f79
Source dataset
uspto-grants-1998_04
Patent number
US05744488

Reaction notes

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