Pyrazole → HCID 86681319, compound

HRID 1430286Notes

Reaction equation

HRID 1430286 reaction equation
[CH:1]1(/[CH:7]=[CH:8]/[CH:9]=[O:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.FC(F)(F)C1C=C(C(C2C=C(C(F)(F)F)C=C(C(F)(F)F)C=2)(O[Si](C)(C)C)C2CCCN2)C=C(C(F)(F)F)C=1.[N+](C1C=CC(C(O)=O)=CC=1)([O-])=O.[NH:62]1[CH:66]=[CH:65][CH:64]=[N:63]1>C1(C)C=CC=CC=1>[CH:1]1([CH:7]([N:62]2[CH:66]=[CH:65][CH:64]=[N:63]2)[CH2:8][CH:9]=[O:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 1048PyrazoleHCID 61084-Nitrobenzoic AcidHCID 11768643HCID 11768643, compoundHCID 59420170HCID 59420170, compound

Product 1

HCID 86681319HCID 86681319, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of (E)-3-cyclohexylacrylaldehyde (4.94 g) (made according to Organic Letters (2011), 13(1), 70-73), 2-(bis(3,5-bis(trifluoromethyl)phenyl)-(trimethylsilyloxy)methyl)pyrrolidine (0.712 g) and 4-nitrobenzoic acid (0.124 mL) in toluene (60 mL) was stirred at room temperature for 10 minutes and 1H-pyrazole (1.622 g) was added. The reaction mixture was stirred for 3 days, and purified by flash chromotography (silica gel, 0-50% ethyl acetate/hexanes).

Workup

  1. custompurified by flash chromotography (silica gel, 0-50% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-6d5cae28791d45729f326f142e31e554
Source dataset
uspto-grants-2015_01
Patent number
US08940737B2

Reaction notes

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