Toluene → 5-Methyl-1-[2'-(trifluoromethoxy)-1,1'-biphenyl-3-yl]-1H-pyrazole-3-carbaldehyde

HRID 733139Notes

Reaction equation

HRID 733139 reaction equation
C([O:3][C:4]([C:6]1[CH:10]=[C:9]([CH3:11])[N:8]([C:12]2[CH:13]=[C:14]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[O:24][C:25]([F:28])([F:27])[F:26])[CH:15]=[CH:16][CH:17]=2)[N:7]=1)=O)C.CC(C[AlH]CC(C)C)C.C1(C)C=CC=CC=1>ClCCl>[CH3:11][C:9]1[N:8]([C:12]2[CH:13]=[C:14]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[O:24][C:25]([F:27])([F:28])[F:26])[CH:15]=[CH:16][CH:17]=2)[N:7]=[C:6]([CH:4]=[O:3])[CH:10]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 14487Diisobutylaluminum hydrideHCID 11417896Ethyl-5-methyl-1-[2'-(trifluoromethoxy)-1,1'-biphenyl-3-yl]-1H-pyrazole-3-carboxylate

Product 1

HCID 114279565-Methyl-1-[2'-(trifluoromethoxy)-1,1'-biphenyl-3-yl]-1H-pyrazole-3-carbaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of ethyl 5-methyl-1-[2′-(trifluoromethoxy)-1,1′-biphenyl-3-yl]-1H-pyrazole-3-carboxylate (from EXAMPLE 3) (1.1 g, 2.82 mmol) in anhydrous dichloromethane (10 mL) was added DIBAL-H in toluene solution (1.0M, 6.8 mL, 6.8 mmol) at −78° C. After stirring for 20 min at that temperature, the reaction was quenched with methanol as described above in EXAMPLE 123. Further work-up and purification, as described in EXAMPLE 123, produced the titled compound.

Workup

  1. customthe reaction was quenched with methanol
  2. customFurther work-up and purification

Sources & evidence

ORD record
ord-088f0fb69e4e4491862a32b7665f4a60
Source dataset
uspto-grants-2009_09
Patent number
US07589116B2

Reaction notes

Loading…