Tetrabutylammonium Fluoride → HCID 57911421, compound

HRID 1099169Notes

Reaction equation

HRID 1099169 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-cd10c80483294e8f96f91ddc6c593faf
Source dataset
uspto-grants-2012_03
Patent number
US08143403B2

Reaction notes

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