Tetrabutylammonium Fluoride → HCID 86679092, compound

HRID 1183358Notes

Reaction equation

HRID 1183358 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][N:11]=[C:10]([CH3:13])[C:9]=2[CH:14]([NH:21][S:22]([CH3:25])(=[O:24])=[O:23])[C:15]#[C:16][Si](C)(C)C)=[CH:4][CH:3]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[O:12][N:11]=[C:10]([CH3:13])[C:9]=2[CH:14]([NH:21][S:22]([CH3:25])(=[O:24])=[O:23])[C:15]#[CH:16])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 66577713HCID 66577713, compound

Product 1

HCID 86679092HCID 86679092, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

N-{1-[5-(4-Bromo-phenyl)-3-methyl-isoxazol-4-yl]-3-trimethylsilanyl-prop-2-ynyl}-methanesulfonamide (from previous step) was dissolved in THF (10 mL) and the mixture was cooled to 0° C. Tetrabutylammonium fluoride (1.0M in THF, 0.3 mL, 0.3 mmol) was added and the reaction stirred at 0° C. for 1 hour. The reaction was then submitted to standard aqueous workup and purified on silica gel (0-70% EtOAc in hexanes) to afford the title compound.

Workup

  1. custompurified on silica gel (0-70% EtOAc in hexanes)

Sources & evidence

ORD record
ord-73b3c1d4e2e044f8be2af45a2ece7e58
Source dataset
uspto-grants-2014_03
Patent number
US08664220B2

Reaction notes

Loading…