Water → HCID 67438408, compound

HRID 1890261Notes

Reaction equation

HRID 1890261 reaction equation
Cl[CH2:2][CH2:3][N:4]1[C:8]([CH2:9][OH:10])=[CH:7][C:6]([C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=2)=[N:5]1.[H-].[Na+].O>CN(C)C=O>[F:17][C:14]1[CH:15]=[CH:16][C:11]([C:6]2[CH:7]=[C:8]3[CH2:9][O:10][CH2:2][CH2:3][N:4]3[N:5]=2)=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 962WaterHCID 24758Sodium hydrideHCID 67436691HCID 67436691, compound

Product 1

HCID 67438408HCID 67438408, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

In a 100 ml round-bottom flask, 780 mg (3.00 mmol) of [1-(2-chloroethyl)-3-(4-fluorophenyl)-1H-pyrazol-5-yl]methanol are dissolved in 20 ml of N,N-dimethylformamide. Under argon and at 0° C., 120 mg of sodium hydride (3.00 mmol) are then added as a 60% suspension in oil. The mixture is then stirred at 25° C. for 18 h. The reaction mixture is then carefully poured into water and extracted repeatedly with ethyl acetate. The combined organic phases are then dried over Na2SO4 and concentrated. Purification is carried out by silica gel chromatography (cyclohexane/ethyl acetate). This gives 480 mg (49%) of the desired product; log P(HCOOH): 2.01; 1H-NMR (MeCN-d3): δ=7.81-7.77 (m, 2H), 7.15-7.11 (m, 2H), 6.36 (s, 1H), 4.81 (s, 2H), 4.14-4.12 (m, 2H), 4.10-4.08 (m, 2H).

Workup

  1. extractionextracted repeatedly with ethyl acetate
  2. dry with materialThe combined organic phases are then dried over Na2SO4
  3. concentrationconcentrated
  4. customPurification

Sources & evidence

ORD record
ord-919c50bbc50748d2899356945ba148d4
Source dataset
uspto-grants-2013_08
Patent number
US08507472B2

Reaction notes

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