Tetrabutylammonium Fluoride → HCID 57911421, compound

HRID 1666136Notes

Reaction equation

HRID 1666136 reaction equation
[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C:9]1=[CH:10][C:11]2[C:12]([CH:17]([O:20][Si](C(C)C)(C(C)C)C(C)C)[CH2:18][CH2:19]1)=[N:13][CH:14]=[CH:15][CH:16]=2.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C:9]1=[CH:10][C:11]2[C:12]([CH:17]([OH:20])[CH2:18][CH2:19]1)=[N:13][CH:14]=[CH:15][CH:16]=2

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 57911485HCID 57911485, compound

Product 1

HCID 57911421HCID 57911421, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The mixture of (E)-6-(2,3-difluorophenyl)-9-(triisopropylsilyloxy)-8,9-dihydro-7H-cyclohepta[b]pyridine (1.6072 g, 3.74 mmol) and TBAF (7.48 mL, 7.48 mmol) in THF (10 mL) was stirred at room temperature for 1 hour. LCMS showed no more starting material and conversion of the desired product. The solvent was removed via vacuum. The reaction was purified by flash column eluted with ethyl acetate in hexane from 0 to 35% to 50% to afford the desired product as a white solid (0.825 g, 81%). All analytical data matched that of previously described.

Sources & evidence

ORD record
ord-e6af707efd9e49d3a8e57203645e9883
Source dataset
uspto-grants-2011_10
Patent number
US08044043B2

Reaction notes

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