Tetrabutylammonium Fluoride → HCID 57911451, compound

HRID 1666145Notes

Reaction equation

HRID 1666145 reaction equation
CCCC[N+](CCCC)(CCCC)CCCC.[F-].[F:19][C:20]1[CH:25]=[CH:24][C:23]([F:26])=[CH:22][C:21]=1[C:27]1=[CH:28][C:29]2[C:30]([CH:35]([O:38][Si](C(C)C)(C(C)C)C(C)C)[CH2:36][CH2:37]1)=[N:31][CH:32]=[CH:33][CH:34]=2>C1COCC1>[F:19][C:20]1[CH:25]=[CH:24][C:23]([F:26])=[CH:22][C:21]=1[C:27]1=[CH:28][C:29]2[C:30]([CH:35]([OH:38])[CH2:36][CH2:37]1)=[N:31][CH:32]=[CH:33][CH:34]=2

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 57911410HCID 57911410, compound

Product 1

HCID 57911451HCID 57911451, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

TBAF (0.954 mL, 0.954 mmol) was added to the THF (5 mL) solution of (E)-6-(2,5-difluorophenyl)-9-(triisopropylsilyloxy)-8,9-dihydro-7H-cyclohepta[b]pyridine (0.2049 g, 0.477 mmol) at rt. The reaction was stirred at room temperature for 6 hours. The solvent was removed via vacuum and the product was purified by flash column eluted with ethyl acetate in hexane from 0 to 50% to 100% (102.2 mg, 78%). MS(ESI)[M+H+]=274.23 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 8.37 (dd, J=4.78, 1.26 Hz, 1 H) 7.51 (dd, J=7.81, 1.26 Hz, 1 H) 7.17-7.27 (m, 1 H) 6.87-7.05 (m, 3 H) 6.44 (s, 1 H) 5.74 (br.s., 1 H) 4.77 (dd, J=10.45, 2.64 Hz, 1 H) 2.79-2.93 (m, 1 H) 2.66-2.77 (m, 1 H) 2.48-2.60 (m, J=13.53, 5.45, 5.45, 2.77 Hz, 1 H) 1.97 -2.11 (m, 1 H).

Workup

  1. customThe solvent was removed via vacuum
  2. customthe product was purified by flash column
  3. washeluted with ethyl acetate in hexane from 0 to 50% to 100% (102.2 mg, 78%)

Sources & evidence

ORD record
ord-e89f76854b5c4417a339482e459ed25e
Source dataset
uspto-grants-2011_10
Patent number
US08044043B2

Reaction notes

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