Diethyl Ether → Ethyl 2-(5-Bromo-7-isopropyl-1H-indol-3-yl)-2-oxoacetate

HRID 2249563Notes

Reaction equation

HRID 2249563 reaction equation
[C:1](Cl)(=[O:5])[C:2](Cl)=[O:3].ClCCl.[Br:10][C:11]1[CH:12]=[C:13]2[C:17](=[C:18]([CH:20]([CH3:22])[CH3:21])[CH:19]=1)[NH:16][CH:15]=[CH:14]2.[CH3:23][CH2:24][O:25]CC>>[Br:10][C:11]1[CH:12]=[C:13]2[C:17](=[C:18]([CH:20]([CH3:22])[CH3:21])[CH:19]=1)[NH:16][CH:15]=[C:14]2[C:1](=[O:5])[C:2]([O:25][CH2:24][CH3:23])=[O:3]

Participants

5

Reactant 4

HCID 3283Diethyl EtherHCID 6344DichloromethaneHCID 65578Oxalyl chlorideHCID 59639728HCID 59639728, compound

Product 1

HCID 59639726Ethyl 2-(5-Bromo-7-isopropyl-1H-indol-3-yl)-2-oxoacetateYield 67%

Procedure

A 2.0 M solution of oxalyl dichloride in dichloromethane (60 ml, 0.12mol) was added dropwise during 10 min to a solution of 5-Bromo-7-isopropyl-1H-indole (14.5 g, 0.061 mol) in Et2O (220 ml) at room temperature under a nitrogen atmosphere. The mixture was stirred for 4.5 hr. The Et2O was removed by evaporation and absolute EtOH (220 ml) was added. The resulting mixture was stirred at room temperature under a nitrogen atmosphere overnight. The EtOH was evaporated, and EtOAc was added to the residue and washed with sat. NaHCO3 and brine. The organic layers were dried over MgSO4, concentrated, and dried under vaccume to give a crude product (13.8 g, 67%). 1H NMR (300 MHz, CDCl3) δ 8.85 (b, NH), 8.46 (dd, 2H), 7.33 (d, 1H), 4.42 (qrt, 2H), 3.21 (m, 1H), 1.44 (t, 3 H), 1.38 (d, 6H), ESI (+) MS m/e=339 (MH+), ESI (−) MS m/e=337 (MH−).

Workup

  1. customThe Et2O was removed by evaporation and absolute EtOH (220 ml)
  2. additionwas added
  3. stirringThe resulting mixture was stirred at room temperature under a nitrogen atmosphere overnight
  4. customThe EtOH was evaporated
  5. additionEtOAc was added to the residue
  6. washwashed with sat. NaHCO3 and brine
  7. dry with materialThe organic layers were dried over MgSO4
  8. concentrationconcentrated
  9. customdried under vaccume

Sources & evidence

ORD record
ord-a5ab5b8027524fe084e7726fc847be06
Source dataset
uspto-grants-2008_01
Patent number
US07314886B2

Reaction notes

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