Chloroform → HCID 66887014, compound

HRID 1043469Notes

Reaction equation

HRID 1043469 reaction equation
[Br:1][C:2]1[C:3]([CH:8]([F:10])[F:9])=[N:4][NH:5][C:6]=1[CH3:7].C(Cl)(Cl)Cl.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[O:27]1[CH:32]=[CH:31][CH2:30][CH2:29][CH2:28]1>>[Br:1][C:2]1[C:3]([CH:8]([F:10])[F:9])=[N:4][N:5]([CH:28]2[CH2:29][CH2:30][CH2:31][CH2:32][O:27]2)[C:6]=1[CH3:7]

Participants

5

Reactant 4

HCID 6212ChloroformHCID 80803,4-dihydro-2H-pyranHCID 521998p-Toluenesulfonic acid monohydrateHCID 668871554-bromo-3-(difluoromethyl)-5-methyl-1H-pyrazole

Product 1

HCID 66887014HCID 66887014, compound

Conditions

Temperature
25 °C

Procedure

To a solution of 4-bromo-3-(difluoromethyl)-5-methyl-1H-pyrazole (1.40 g, 6.63 mmol) in chloroform (30.0 mL, 0.375 mol) was added p-toluenesulfonic acid monohydrate (0.13 g, 0.66 mol) at 0° C. Dihydropyran (0.91 mL, 0.010 mol) was added and stirred at 25° C. for 2 h. The reaction was extracted with ethyl acetate and the organic extracts were washed with NaHCO3, water, saturated NaCl, dried (MgSO4) and concentrated in vacuo. The compound was chromatographed on silica gel using 10% EtOAc/hexanes to give the desired product. 1H NMR (CDCl3): δ 6.51-6.78 (t, 1H), 5.31 (dd, 1H), 4.01 (m, 1H), 3.65 (m, 1H), 2.40 (m, 1H), 2.35 (s, 3H), 2.21 (m, 1H), 1.95 (m, 1H), 1.50-1.70 (m, 3H).

Workup

  1. extractionThe reaction was extracted with ethyl acetate
  2. washthe organic extracts were washed with NaHCO3, water, saturated NaCl
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customThe compound was chromatographed on silica gel using 10% EtOAc/hexanes

Sources & evidence

ORD record
ord-76bfaffcb68649208f23b68bdcd5faff
Source dataset
uspto-grants-2013_10
Patent number
US08563541B2

Reaction notes

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