Tetrabutylammonium Fluoride → HCID 178436941, compound

HRID 2105018Notes

Reaction equation

HRID 2105018 reaction equation
[Br:1][C:2]1[N:3]=[C:4]([CH:7]([C:9]2[CH:14]=[C:13]([CH2:15][CH3:16])[CH:12]=[C:11]([O:17][Si](C(C)(C)C)(C)C)[C:10]=2[F:25])[OH:8])[NH:5][CH:6]=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[Br:1][C:2]1[N:3]=[C:4]([CH:7]([OH:8])[C:9]2[C:10]([F:25])=[C:11]([OH:17])[CH:12]=[C:13]([CH2:15][CH3:16])[CH:14]=2)[NH:5][CH:6]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 178436971HCID 178436971, compound

Product 1

HCID 178436941HCID 178436941, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of intermediate 206.1 (500 mg, 0.744 mmol) in 7 mL THF at 0° C., was added TBAF (1M in THF, 0.744 mL, 0.744 mmol). The mixture was stirred at 0° C. for 30 min, then concentrated. The mixture was diluted with EtOAc, washed with H2O (2×) and brine, dried (Na2SO4) and concentrated. The crude product was triturated with 10% EtOAc/hexanes (10 mL) to afford after filtration 399 mg of Intermediate 191.2 as a white powder. LCMS (2 min gradient) RT=2.18 min, 579.13 (M+Na)+.

Workup

  1. concentrationconcentrated
  2. additionThe mixture was diluted with EtOAc
  3. washwashed with H2O (2×) and brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customThe crude product was triturated with 10% EtOAc/hexanes (10 mL)
  7. customto afford
  8. filtrationafter filtration 399 mg of Intermediate 191.2 as a white powder
  9. customLCMS (2 min gradient) RT=2.18 min, 579.13 (M+Na)+

Sources & evidence

ORD record
ord-1f00c6696aee4d8ead6a117e0e0fb7f2
Source dataset
uspto-grants-2009_08
Patent number
US07576098B2

Reaction notes

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