Trifluoroacetic acid → HCID 136159881, compound

HRID 2061412Notes

Reaction equation

HRID 2061412 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:9]([N:11]2[CH2:15][CH2:14][C:13]([C:16]3[CH:21]=[C:20]([Br:22])[C:19]([O:23]CC4C=CC(OC)=CC=4)=[C:18]([Br:33])[CH:17]=3)=[N:12]2)=[O:10])[CH:5]=[CH:6][C:7]=1[Cl:8].FC(F)(F)C(O)=O>ClCCl>[Br:1][C:2]1[CH:3]=[C:4]([C:9]([N:11]2[CH2:15][CH2:14][C:13]([C:16]3[CH:21]=[C:20]([Br:22])[C:19]([OH:23])=[C:18]([Br:33])[CH:17]=3)=[N:12]2)=[O:10])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59829174HCID 59829174, compound

Product 1

HCID 136159881HCID 136159881, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of (3-bromo-4-chlorophenyl)(3-(3,5-dibromo-4-(4-methoxybenzyloxy)phenyl)-4,5-dihydro-1H-pyrazol-1-yl)methanone (F) (51.8 mg, 0.0788 mmol) in anhydrous dichloromethane (5 ml) under nitrogen was added trifluoroacetic acid (0.1 mL) and the solution was stirred at room temperature for 1 h 40 min. The solvent was evaporated and more dichloromethane was added to the residue and evaporated. The residue was then recrystallised from EtOAc-CH2Cl2 and the resulting solid was collected by filtration, washed with 50% EtOAc/pet. ether and dried at 55° C. under vacuum to leave 28.2 mg (67%) of the title compound as a light-brown solid. 1H NMR δ (ppm) (DMSO-d6): 4.13 (2 H, t, J=9.8 Hz), 7.81 (1 H, d, J=8.4 Hz), 7.86 (2 H, s), 7.86-7.93 (1 H, m), 8.24 (1 H, d, J=2.0 Hz), 10.62 (1 H, br s). LCMS (10 cm_apci_formic) Rt 4.29 min; m/z 535/537/539/541/543 [M+H].

Workup

  1. customThe solvent was evaporated
  2. additionmore dichloromethane was added to the residue
  3. customevaporated
  4. customThe residue was then recrystallised from EtOAc-CH2Cl2
  5. filtrationthe resulting solid was collected by filtration
  6. washwashed with 50% EtOAc/pet. ether
  7. customdried at 55° C. under vacuum

Sources & evidence

ORD record
ord-e9e66b1415244792bfcaaa7b29be1952
Source dataset
uspto-grants-2012_10
Patent number
US08283351B2

Reaction notes

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