Tetrabutylammonium Fluoride → HCID 11493084, compound

HRID 1817509Notes

Reaction equation

HRID 1817509 reaction equation
C([Si](C1C=CC=CC=1)(C1C=CC=CC=1)[O:6][C:7]1[CH:8]=[C:9]([C:13]([C:15]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[N:17]([CH2:24][CH:25]([CH3:27])[CH3:26])[N:16]=2)=[O:14])[CH:10]=[CH:11][CH:12]=1)(C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[OH:6][C:7]1[CH:8]=[C:9]([C:13]([C:15]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[N:17]([CH2:24][CH:25]([CH3:27])[CH3:26])[N:16]=2)=[O:14])[CH:10]=[CH:11][CH:12]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 69065596HCID 69065596, compound

Product 1

HCID 11493084HCID 11493084, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

[3-(tert-Butyl-diphenyl-silanyloxy)-phenyl]-(1-isobutyl-1H-indazol-3-yl)-methanone (0.650 g, 0.0012 mol) was dissolved in dry THF (1 mL) in a glass vial. The vial was cooled to −78 C in a dry ice/acetone bath. TBAF (1.8 mL of a 1 M soln., 0.0018 mol) was added. The vial was removed from the bath and stirred until a dark yellow color persisted (approx. 1 minute). The vial was placed back in the bath and the progress of the reaction was followed by TLC. When complete, the reaction was quenched with aqueous HCl (1-2N), adsorbed on a small plug of silica gel, and chromatographed with hexane/ethyl acetate (10:1) to give the desired product.

Workup

  1. temperatureThe vial was cooled to −78 C in a dry ice/acetone bath
  2. addition, 0.0018 mol) was added
  3. customThe vial was removed from the bath
  4. custom(approx. 1 minute)
  5. customWhen complete, the reaction was quenched with aqueous HCl (1-2N)
  6. customchromatographed with hexane/ethyl acetate (10:1)

Sources & evidence

ORD record
ord-d08f4c736b684633938a486659847b30
Source dataset
uspto-grants-2009_10
Patent number
US07598286B2

Reaction notes

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