Water → {2-[1-(2,6-Dichloro-4-trifluoromethylphenyl)-3,5-diethyl-1H-pyrazol-4-ylmethyl]-1,2,3,4-tetrahydroisoquinolin-3-yl}methanol

HRID 619311Notes

Reaction equation

HRID 619311 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[C:4]([Cl:12])[C:3]=1[N:13]1[C:17]([CH2:18][CH3:19])=[C:16]([CH2:20]O)[C:15]([CH2:22][CH3:23])=[N:14]1.C([N:26]([CH2:29][CH3:30])[CH2:27][CH3:28])C.CS(Cl)(=O)=O.[C:36](#N)[CH3:37].[OH2:39]>C(Cl)Cl.C(OCC)(=O)C.CN(C)C=O>[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:10])([F:9])[F:11])[CH:5]=[C:4]([Cl:12])[C:3]=1[N:13]1[C:17]([CH2:18][CH3:19])=[C:16]([CH2:20][N:26]2[CH:27]([CH2:28][OH:39])[CH2:37][C:36]3[C:30](=[CH:7][CH:2]=[CH:3][CH:4]=3)[CH2:29]2)[C:15]([CH2:22][CH3:23])=[N:14]1

Participants

9

Reactant 5

HCID 962WaterHCID 6342AcetonitrileHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 21837337[1-(2,6-dichloro-4-trifluoromethylphenyl)-3,5-diethyl-1H-pyrazol-4-yl]methanol

Product 1

HCID 54199408{2-[1-(2,6-Dichloro-4-trifluoromethylphenyl)-3,5-diethyl-1H-pyrazol-4-ylmethyl]-1,2,3,4-tetrahydroisoquinolin-3-yl}methanolYield 45%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
2.5 °C

Procedure

A solution of 368 mg (1.0 mmol) of [1-(2,6-dichloro-4-trifluoromethylphenyl)-3,5-diethyl-1H-pyrazol-4-yl]methanol in 10 mL of methylene chloride and 0.2 mL (2.5 mmol) of triethylamine was cooled to 0-5° C. To this was added 0.92 mL (1.2 mmol) of methanesulfonyl chloride and the reaction mixture was stirred at 0-5 ° C. for 15 minutes. Then 1 mL of acetonitrile and 1 mL of dimethylformamide was added and the reaction mixture was heated at reflux overnight. The cooled reaction mixture was taken up with water and with ethyl acetate and the organic extracts were dried and evaporated to an orange oil which was purified by flash chromatography to give the desired product in 45% yield. 1H-NMR (CDCl3) δ0.86 (3H, t, J=7), 1.21 (3H, t, J=7), 2.28 (2H, q, J=7), 2.60 (2H, q, J=7), 2.92-3.04 (1H, m), 3.20-3.32 (1H, m), 3.50-3.90 7H, m), 6.90-7.24 (4H, m), 7.68 (2H, s).

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux overnight
  3. customThe cooled reaction mixture
  4. customthe organic extracts were dried
  5. customevaporated to an orange oil which
  6. customwas purified by flash chromatography

Sources & evidence

ORD record
ord-f8590d7de66240afb19570e06a52f0fb
Source dataset
uspto-grants-1999_09
Patent number
US05958948

Reaction notes

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