Sodium Bicarbonate → [4-(1-Methyl-4-pyridin-4-yl-1H-pyrazol-3-yl)-phenyl]-methanol

HRID 33912Notes

Reaction equation

HRID 33912 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[CH:12]=[CH:11][N:10]=[CH:9][CH:8]=2)[C:4]([C:13]2[CH:18]=[CH:17][C:16]([CH2:19][O:20][Si](C(C)C)(C(C)C)C(C)C)=[CH:15][CH:14]=2)=[N:3]1.CCCC[N+](CCCC)(CCCC)CCCC.[F-].C(=O)(O)[O-].[Na+]>C1COCC1>[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[CH:8]=[CH:9][N:10]=[CH:11][CH:12]=2)[C:4]([C:13]2[CH:18]=[CH:17][C:16]([CH2:19][OH:20])=[CH:15][CH:14]=2)=[N:3]1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 2724141Tetrabutylammonium FluorideHCID 685782264-[1-Methyl-3-(4-triisopropylsilanyloxymethyl-phenyl)-1H-pyrazol-4-yl]-pyridine

Product 1

HCID 68575885[4-(1-Methyl-4-pyridin-4-yl-1H-pyrazol-3-yl)-phenyl]-methanolYield 84%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-[1-Methyl-3-(4-triisopropylsilanyloxymethyl-phenyl)-1H-pyrazol-4-yl]-pyridine (1.75 g) in THF (16.2 mL) was added TBAF (1.0M THF, 5.2 mL) and the reaction mixture stirred at ambient temperature under inert atmosphere for 1 h. The reaction mixture was poured into saturated sodium bicarbonate, extracted 3× with chloroform, dried magnesium sulfate filtered and concentration. Purification via MPLC biotage chromatography eluting with 2% methanol/0.5% saturated ammonium hydroxide/50% ethyl acetate/hexanes provided the title compound (920 mg, 84%). MS: (M+H m/z=266.1).

Workup

  1. extractionextracted 3× with chloroform, dried magnesium sulfate
  2. filtrationfiltered
  3. concentrationconcentration
  4. customPurification via MPLC biotage chromatography
  5. washeluting with 2% methanol/0.5% saturated ammonium hydroxide/50% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-daf2de28e4a04224a4ec76de83b7d7fb
Source dataset
uspto-grants-2008_09
Patent number
US07429665B2

Reaction notes

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