Hydrochloric Acid → 2-[4-({4-[2-Benzyl-7-(trifluoromethyl)-2H-indazol-3-YL]phenoxy}methyl)phenyl]propanoic acid

HRID 735475Notes

Reaction equation

HRID 735475 reaction equation
[CH2:1]([N:8]1[C:16]([C:17]2[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=2)=[C:15]2[C:10]([C:11]([C:24]([F:27])([F:26])[F:25])=[CH:12][CH:13]=[CH:14]2)=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH2:29][C:30]1[CH:35]=[CH:34][C:33]([CH:36]([CH3:40])[C:37]([OH:39])=[O:38])=[CH:32][CH:31]=1.C(=O)([O-])[O-].[K+].[K+].Cl>CN(C=O)C.O>[CH2:1]([N:8]1[C:16]([C:17]2[CH:22]=[CH:21][C:20]([O:23][CH2:29][C:30]3[CH:31]=[CH:32][C:33]([CH:36]([CH3:40])[C:37]([OH:39])=[O:38])=[CH:34][CH:35]=3)=[CH:19][CH:18]=2)=[C:15]2[C:10]([C:11]([C:24]([F:27])([F:25])[F:26])=[CH:12][CH:13]=[CH:14]2)=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 27339782-[4-(Bromomethyl)phenyl]propanoic acidHCID 136393280HCID 136393280, compound

Product 1

HCID 670212092-[4-({4-[2-Benzyl-7-(trifluoromethyl)-2H-indazol-3-YL]phenoxy}methyl)phenyl]propanoic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

The title compound was prepared by treating 4-(2-benzyl-7-trifluoromethyl-2H-indazole-3-yl)-phenol (20 mg, 1 eq) with 2-(4-bromomethyl-phenyl)-propionic acid (39 mg, 3 eq) and potassium carbonate (37 mg, 5 eq) in DMF (2 mL) at 150° C. overnight. After cooling, water was added and the pH adjusted to 1 (aq. HCl, 2M) followed by extraction with dichloromethane. Purification by preparative HPLC gave the desired product in 45% yleld.

Workup

  1. customThe title compound was prepared
  2. temperatureAfter cooling
  3. extractionfollowed by extraction with dichloromethane
  4. customPurification by preparative HPLC

Sources & evidence

ORD record
ord-9c5e116b6417415381699154327b0592
Source dataset
uspto-grants-2009_09
Patent number
US07592363B2

Reaction notes

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