Diethyl Ether → HCID 68659485, compound

HRID 1945309Notes

Reaction equation

HRID 1945309 reaction equation
CC(C[AlH]CC(C)C)C.[Br:10][C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][C:19]=1[F:20])[N:16]([CH2:21][C:22](OCC)=[O:23])[CH:15]=[CH:14]2.[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+].CCOCC>C1COCC1>[Br:10][C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][C:19]=1[F:20])[N:16]([CH2:21][CH2:22][OH:23])[CH:15]=[CH:14]2

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 9357Potassium Sodium TartrateHCID 14487Diisobutylaluminum hydrideHCID 86640506Ethyl 5-bromo-6-fluoro-1H-indole-1-acetate

Product 1

HCID 68659485HCID 68659485, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

DIBAL-H (1 M in hexanes) (4 mL, 4 mmol) was added to a 0° C. solution of ethyl (5-bromo-6-fluoro-1H-indol-1-yl)acetate (0.480 g, 1.60 mmol) in anhydrous THF (10 mL). The reaction was stirred at rt for 1 h, then treated with saturated aqueous Rochelle's salt and Et2O. The mixture was stirred vigorously for 30 min. The layers were separated and the aqueous layer was further extracted with Et2O. The combined organic layers were washed with brine, dried (Na2SO4), filtered, and concentrated. Chromatography over silica eluting with 60% EtOAc/hexanes afforded the desired compound as an oil.

Workup

  1. stirringThe mixture was stirred vigorously for 30 min
  2. customThe layers were separated
  3. extractionthe aqueous layer was further extracted with Et2O
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-66a680f25bcd45f598b9c183f3dfec6c
Source dataset
uspto-grants-2013_03
Patent number
US08394969B2

Reaction notes

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