Tetrabutylammonium Fluoride → HCID 15604426, compound

HRID 1784822Notes

Reaction equation

HRID 1784822 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]([C:9]2[CH:14]=[C:13]([O:15][Si](C(C)C)(C(C)C)C(C)C)[CH:12]=[C:11]([C:26]3[CH:34]=[CH:33][CH:32]=[C:31]4[C:27]=3[CH:28]=[CH:29][N:30]4[Si](C(C)C)(C(C)C)C(C)C)[CH:10]=2)=[O:8])[CH:2]=1.[CH3:45][Mg]Cl.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1.[Cl-].[Na+].O>[OH:8][C:7]([C:9]1[CH:14]=[C:13]([OH:15])[CH:12]=[C:11]([C:26]2[CH:34]=[CH:33][CH:32]=[C:31]3[C:27]=2[CH:28]=[CH:29][NH:30]3)[CH:10]=1)([C:3]1[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=1)[CH3:45]

Participants

6

Reactant 3

HCID 2724141Tetrabutylammonium FluorideHCID 68843505HCID 68843505, compoundHCID 178418332HCID 178418332, compound

Product 1

HCID 15604426HCID 15604426, compoundYield 39%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 57417360Sodium chloride; waterSolvent

Procedure

To pyridin-3-yl-[3-(1-triisopropylsilanyl-1H-indol-4-yl)-5-triisopropylsilanyloxy-phenyl]-methanone (64 mg, 0.102 mmol) in 2 mL of THF was added 2 mL of MeMgCl (1 M in THF) at 0° C. After 30 min TLC indicated the completion of the reaction. Brine was then added to quench the reaction. The aqueous phase was then extracted with EtOAc. The combined organic phases were dried and concentrated to afford the crude product. The residue was again dissolved in 2 mL of THF and followed by addition of 1 mL of TBAF (3M in THF) at 0° C. After 30 min the solvent of the reaction was removed under reduced pressure. The residue was dissolved in EtOAc and the organic phase washed with water and brine, dried and concentrated to afford the crude product. The crude product was then purified by prep. TLC to afford 3-(1-hydroxy-1-pyridin-3-yl-ethyl)-5-(1H-indol-4-yl)-phenol (13 mg, 39% over two steps). 1H NMR (400 MHz, CD3OD): δ 8.66 (d, 1H, J=1.6 Hz), 8.36 (d, 1H, J=4.0 Hz), 7.93 (d, 1H, J=6.4 Hz), 7.36 (dd, 1H, J=8.0, 4.8 Hz), 7.33 (d, 1H, J=8.0 Hz), 7.21 (d, 1H, J=2.8 Hz), 7.20-7.19 (m, 1H), 7.11 (t, 1H, J=8.0 Hz), 7.01 (d, 1H, J=7.2 Hz), 6.99-6.98 (m, 1H), 6.99 (t, 1H, J=1.6 Hz), 6.46 (d, 1H, J=3.6 Hz), 1.98 (s, 3H).

Workup

  1. customthe completion of the reaction
  2. customto quench
  3. customthe reaction
  4. extractionThe aqueous phase was then extracted with EtOAc
  5. customThe combined organic phases were dried
  6. concentrationconcentrated
  7. customto afford the crude product
  8. customAfter 30 min the solvent of the reaction was removed under reduced pressure
  9. dissolutionThe residue was dissolved in EtOAc
  10. washthe organic phase washed with water and brine
  11. customdried
  12. concentrationconcentrated
  13. customto afford the crude product
  14. customThe crude product was then purified by prep

Sources & evidence

ORD record
ord-ee78f4f15c7742d89b86ba8906c4996d
Source dataset
uspto-grants-2009_03
Patent number
US07504401B2

Reaction notes

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