Tetrabutylammonium Fluoride → 4-[(5-Methyl-3-{3-[4-(trifluoromethoxy)phenyl]-1,2,4-oxadiazol-5-yl}-1H-pyrazol-1-yl)-methyl]phenol

HRID 2400589Notes

Reaction equation

HRID 2400589 reaction equation
[CH3:1][C:2]1[N:6]([CH2:7][C:8]2[CH:13]=[CH:12][C:11]([O:14][Si](C(C)C)(C(C)C)C(C)C)=[CH:10][CH:9]=2)[N:5]=[C:4]([C:25]2[O:29][N:28]=[C:27]([C:30]3[CH:35]=[CH:34][C:33]([O:36][C:37]([F:40])([F:39])[F:38])=[CH:32][CH:31]=3)[N:26]=2)[CH:3]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[CH3:1][C:2]1[N:6]([CH2:7][C:8]2[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=2)[N:5]=[C:4]([C:25]2[O:29][N:28]=[C:27]([C:30]3[CH:35]=[CH:34][C:33]([O:36][C:37]([F:40])([F:38])[F:39])=[CH:32][CH:31]=3)[N:26]=2)[CH:3]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 595047665-[5-Methyl-1-(4-{[tris(1-methylethyl)silyl]oxy}benzyl)-1H-pyrazol-3-yl]-3-[4-(trifluoromethoxy)phenyl]-1,2,4-oxadiazole

Product 1

HCID 585616274-[(5-Methyl-3-{3-[4-(trifluoromethoxy)phenyl]-1,2,4-oxadiazol-5-yl}-1H-pyrazol-1-yl)-methyl]phenol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-[5-methyl-1-(4-{[tris(1-methylethyl)silyl]oxy}benzyl)-1H-pyrazol-3-yl]-3-[4-(trifluoromethoxy)phenyl]-1,2,4-oxadiazole (Step 1, 500 mg, 0.873 mmol) in THF (20 mL) was added a solution of tetrabutylammonium fluoride (1M in THF, 960 μl, 0.96 mmol) at a temperature of 0° C. The cooling bath was removed, and the reaction mixture was stirred at rt for 1 h. After the addition of water (100 μL), most of the organic solvent was removed in vacuo and replaced by methanol (1 mL). The crude mixture was subjected to preparative HPLC to afford the title compound in pure form (416 mg, 67%): 1H NMR (400 MHz, CDCl3) 8.24 (d, 2H), 7.32 (d, 2H), 7.07 (d, 2H), 6.79 (d, 2H), 6.78 (s, 1H), 5.61 (broad, 1H), 5.35 (s, 2H), 2.28 (s, 3H); ES-MS m/z 417, HPLC RT (Method J) 4.78 min.

Workup

  1. customThe cooling bath was removed
  2. additionAfter the addition of water (100 μL)
  3. custommost of the organic solvent was removed in vacuo

Sources & evidence

ORD record
ord-c2726e24972240c29bae396a8791427a
Source dataset
uspto-grants-2014_08
Patent number
US08796253B2

Reaction notes

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