Tetrahydrofuran → 1H-Indole-7-carboxaldehyde, 6-fluoro-2,3-dihydro-

HRID 557224Notes

Reaction equation

HRID 557224 reaction equation
C([Li])(C)(C)C.C(OC([N:13]1[C:21]2[C:16](=[CH:17][CH:18]=[C:19]([F:22])[CH:20]=2)[CH2:15][CH2:14]1)=O)(C)(C)C.[O:23]1CCC[CH2:24]1>>[F:22][C:19]1[C:20]([CH:24]=[O:23])=[C:21]2[C:16]([CH2:15][CH2:14][NH:13]2)=[CH:17][CH:18]=1

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 17985580Tert-butyl 6-fluoroindoline-1-carboxylateHCID 178418306HCID 178418306, compound

Product 1

HCID 179858381H-Indole-7-carboxaldehyde, 6-fluoro-2,3-dihydro-Yield 42%

Procedure

Add tert-butyllithium (21.13 ml, 35.93 mmol, 1.7 M solution in heptane) to a solution of 1-(tert-butoxycarbonyl)-2,3-dihydro-6-fluoroindole (3.28 g, 13.82 mmol) in anhydrous tetrahydrofuran (100 ml) at −78 C. Stir for 20 minutes, quench with excess dimethylformamide, and stir for 1 hour at −78 C. Warm to room temperature, add saturated aqueous ammonium chloride, and extract with ethyl acetate. Concentrate the combined organic phases under reduced pressure and subject the residue to silica gel chromatography to provide the desired compound as a bright yellow solid (0.91 g, 42%).

Workup

  1. customquench with excess dimethylformamide
  2. stirringstir for 1 hour at −78 C
  3. additionadd saturated aqueous ammonium chloride
  4. extractionextract with ethyl acetate
  5. concentrationConcentrate the combined organic phases under reduced pressure

Sources & evidence

ORD record
ord-d6497d076ccd403bba13a0007ac9ae9f
Source dataset
uspto-grants-2011_11
Patent number
US08058425B2

Reaction notes

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