Tetrabutylammonium Fluoride → HCID 59437290, compound

HRID 244482Notes

Reaction equation

HRID 244482 reaction equation
[Si]([O:8][CH2:9][C:10]1[S:11][CH:12]=[C:13]([C:15]([C:21]2[CH:22]=[C:23]3[C:27](=[CH:28][CH:29]=2)[N:26]([C:30]2[CH:35]=[CH:34][C:33]([F:36])=[CH:32][CH:31]=2)[N:25]=[CH:24]3)([OH:20])[C:16]([F:19])([F:18])[F:17])[N:14]=1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[F:18][C:16]([F:17])([F:19])[C:15]([C:21]1[CH:22]=[C:23]2[C:27](=[CH:28][CH:29]=1)[N:26]([C:30]1[CH:35]=[CH:34][C:33]([F:36])=[CH:32][CH:31]=1)[N:25]=[CH:24]2)([C:13]1[N:14]=[C:10]([CH2:9][OH:8])[S:11][CH:12]=1)[OH:20]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 594372131-[2-(tert-butyldimethylsilanyloxymethyl)thiazol-4-yl]-2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]ethanol

Product 1

HCID 59437290HCID 59437290, compoundYield 97.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a chilled (0° C.) solution of 1-[2-(tert-butyldimethylsilanyloxymethyl)thiazol-4-yl]-2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]ethanol (300 mg, 0.558 mmol) in 15 mL of THF was added tetra-n-butylammonium fluoride (0.670 mL, 1 M solution in THF, 0.67 mmol). The mixture was warmed to room temperature. After 30 minutes, the mixture was quenched with 50 mL of saturated aqueous sodium bicarbonate and extracted with three 50 mL portions of diethyl ether. The combined organic layers were washed with 20 mL of brine, dried over magnesium sulfate, filtered, and concentrated in vacuo. The residue was chromatographed on SiO2 (0-50% ethyl acetate in hexanes) to afford 230 mg (97%) of the title compound. MS m/z 424.71 (MH+).

Workup

  1. customthe mixture was quenched with 50 mL of saturated aqueous sodium bicarbonate
  2. extractionextracted with three 50 mL portions of diethyl ether
  3. washThe combined organic layers were washed with 20 mL of brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was chromatographed on SiO2 (0-50% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-4196d786bad54f7a9d782c1dc2cd07a6
Source dataset
uspto-grants-2014_02
Patent number
US08658637B2

Reaction notes

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