Tetrabutylammonium Fluoride → 3-Morpholin-4-yl-1H-indole

HRID 736972Notes

Reaction equation

HRID 736972 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[N:19]1([C:25]2[C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[N:27]([Si](C(C)C)(C(C)C)C(C)C)[CH:26]=2)[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1>C1COCC1.O>[N:19]1([C:25]2[C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[NH:27][CH:26]=2)[CH2:20][CH2:21][O:22][CH2:23][CH2:24]1

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 589751763-Morpholin-4-yl-1-triisopropylsilanyl-1H-indole

Product 1

HCID 125308333-Morpholin-4-yl-1H-indoleYield 89%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Add 1N solution of tetrabutylammonium fluoride (0.70 mL, 0.70 mmol) to a solution of 3-Morpholin-4-yl-1-triisopropylsilanyl-1H-indole (0.20 g, 0.56 mmol) in THF (2.0 mL). Stir at room temperature for 2 h, dilute with water, and extract with EtOAc. Wash EtOAc with saturated NaHCO3, water, dry (Na2SO4), and concentrate under vacuum. Purify the residue by flash chromatography using 20 to 80% of EtOAc in hexanes to give the title compound (0.10 g 89%). MS (ES) 203.1 (M+1)+.

Workup

  1. extractionextract with EtOAc
  2. dry with materialWash EtOAc with saturated NaHCO3, water, dry (Na2SO4)
  3. concentrationconcentrate under vacuum
  4. customPurify the residue by flash chromatography

Sources & evidence

ORD record
ord-d173c8c61e2746caa10b9abc2f46171d
Source dataset
uspto-grants-2009_09
Patent number
US07595339B2

Reaction notes

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