3,4-dihydro-2H-pyran → HCID 67513852, compound

HRID 473834Notes

Reaction equation

HRID 473834 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:12]=[CH:11][NH:10][N:9]=2)=[CH:4][CH:3]=1.[O:13]1[CH:18]=[CH:17][CH2:16][CH2:15][CH2:14]1>C1(C)C=CC=CC=1.FC(F)(F)C(O)=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:12]=[CH:11][N:10]([CH:14]3[CH2:15][CH2:16][CH2:17][CH2:18][O:13]3)[N:9]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 80803,4-dihydro-2H-pyranHCID 178419346HCID 178419346, compound

Product 1

HCID 67513852HCID 67513852, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 6422Trifluoroacetic acidCatalystHCID 1140TolueneSolvent

Procedure

To a heated (80° C.) solution of 3-(4-bromophenyl)-1H-pyrazole (1.0 g, 4.5 mmol) and trifluoroacetic acid (0.02 mL, 0.23 mmol) in toluene (5 mL) was added 3,4-dihydro-2H-pyran (0.43 mL, 4.7 mol) over 1 hour. The reaction mixture was stirred for an additional hour and was then concentrated and dried to provide 3-(4-bromophenyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazole (1.3 g, 94% yield). MS (EI) for C14H15BrN2O: 308 (MH+).

Workup

  1. concentrationwas then concentrated
  2. customdried

Sources & evidence

ORD record
ord-37cdb9f6c68d4cbf902bf7e2d0177567
Source dataset
uspto-grants-2014_01
Patent number
US08637499B2

Reaction notes

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