Sodium hydride → HCID 15380283, compound

HRID 976570Notes

Reaction equation

HRID 976570 reaction equation
[H-].[Na+].[CH3:3][C:4]1([CH3:24])[CH2:8][O:7][C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[C:15]2[CH:16]=[C:17]3[C:21](=[CH:22][CH:23]=2)[NH:20][CH:19]=[CH:18]3)=[N:5]1.Br[CH:26]([CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])[C:27]([O:29][CH2:30][CH3:31])=[O:28].[Cl-].[NH4+]>C1COCC1>[CH3:3][C:4]1([CH3:24])[CH2:8][O:7][C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[C:15]2[CH:16]=[C:17]3[C:21](=[CH:22][CH:23]=2)[N:20]([CH:26]([CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])[C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH:19]=[CH:18]3)=[N:5]1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 95580Ethyl 2-bromooctanoateHCID 21468894HCID 21468894, compound

Product 1

HCID 15380283HCID 15380283, compoundYield 86.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Sodium hydride (0.54 mmoles, 22 mg of 60% in mineral oil) was added to 5-[2-(4,4-dimethyloxazolin-2-yl)phenyl]indole (0.43 mmoles, 125 mg) in 2 ml THF. After stirring 20 minutes, the solution was cooled to 0° C. Ethyl 2-bromooctanoate (0.54 mmoles, 0.135 mg) was added. The solution was stirred for 15 minutes, allowed to warm to room temperature, and stirred for 1.5 hours. The solution was poured into saturated ammonium chloride and extracted with ethyl acetate. The organic phase was dried and concentrated. The oil was chromatographed over silica gel eluted with 20% ether in hexane. The reaction yielded 172 mg of ethyl 2-[5-[2-(4,4-dimethyloxazolin-2-yl)phenyl]indol-1-yl]octanoate. (MS)

Workup

  1. stirringThe solution was stirred for 15 minutes
  2. temperatureto warm to room temperature
  3. stirringstirred for 1.5 hours
  4. extractionextracted with ethyl acetate
  5. customThe organic phase was dried
  6. concentrationconcentrated
  7. customThe oil was chromatographed over silica gel
  8. washeluted with 20% ether in hexane

Sources & evidence

ORD record
ord-cc040763efcf45b7a2080bb02165b981
Source dataset
uspto-grants-1997_03
Patent number
US05612360

Reaction notes

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