Hydrochloric Acid → (2-(1-(3,3,3-trifluoropropyl)-1H-pyrazol-5-yl)pyridin-3-yl)methanol

HRID 1484768Notes

Reaction equation

HRID 1484768 reaction equation
[Si]([O:8][CH2:9][C:10]1[C:11]([C:16]2[N:20]([CH2:21][CH2:22][C:23]([F:26])([F:25])[F:24])[N:19]=[CH:18][CH:17]=2)=[N:12][CH:13]=[CH:14][CH:15]=1)(C(C)(C)C)(C)C.Cl>CO>[F:26][C:23]([F:24])([F:25])[CH2:22][CH2:21][N:20]1[C:16]([C:11]2[C:10]([CH2:9][OH:8])=[CH:15][CH:14]=[CH:13][N:12]=2)=[CH:17][CH:18]=[N:19]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 866907283-((tert-butyldimethylsilyloxy)methyl)-2-(1-(3,3,3-trifluoropropyl)-1H-pyrazol-5-yl)pyridine

Product 1

HCID 86690730(2-(1-(3,3,3-trifluoropropyl)-1H-pyrazol-5-yl)pyridin-3-yl)methanolYield 99%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 3-((tert-butyldimethylsilyloxy)methyl)-2-(1-(3,3,3-trifluoropropyl)-1H-pyrazol-5-yl)pyridine (1.58 g, 4.1 mmol) in MeOH (20 mL) was added HCl (4 N, 4.0 mL). The mixture was stirred at RT for 1 h, concentrated, and diluted with EtOAc (50 mL) and NaHCO3(sat) solution (10 mL). The layers were separated and aqueous layer was extracted with EtOAc three times. The combined organic layers were dried over Na2SO4, and concentrated to give (2-(1-(3,3,3-trifluoropropyl)-1H-pyrazol-5-yl)pyridin-3-yl)methanol (1.1 g, 99%) as colorless oil. 1H NMR (400 MHz, CDCl3) δ 8.64 (dd, J=4.7, 1.7 Hz, 1H), 8.00 (dd, J=7.9, 1.7 Hz, 1H), 7.57 (d, J=1.9 Hz, 1H), 7.38 (dd, J=7.9, 4.8 Hz, 1H), 6.48 (d, J=1.9 Hz, 1H), 4.69 (s, 2H), 4.51-4.43 (m, 2H), 2.85-2.72 (m, 2H), 2.70 (s, 1H). MS (ESD m/z 272.1 [M+H]+.

Workup

  1. concentrationconcentrated
  2. additiondiluted with EtOAc (50 mL) and NaHCO3(sat) solution (10 mL)
  3. customThe layers were separated
  4. extractionaqueous layer was extracted with EtOAc three times
  5. dry with materialThe combined organic layers were dried over Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-316d96a4c4b04028b58c3752747818a3
Source dataset
uspto-grants-2016_08
Patent number
US09422279B2

Reaction notes

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