Benzyl Bromide → 2-Benzyl-3-[4-(benzyloxy)phenyl]-7-(trifluoromethyl)-2H-indazole

HRID 735474Notes

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.[CH2:28](Br)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:1]([N:8]1[C:16]([C:17]2[CH:22]=[CH:21][C:20]([O:23][CH2:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=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

Conditions

Temperature: 60 °C

Procedure

4-(2-Benzyl-7-trifluoromethyl-2H-indazole-3-yl)-phenol (10 mg, 1 eq) was treated with benzylbromide (10 μL, 3 eq) and potassium carbonate (19 mg, 5 eq) in acetone (1 mL). The reaction mixture was heated at 60° C. until completion of the reaction, as judged by TLC. Volatiles were removed in vacuo and the residue treated with a water/dichloromethane mixture followed by extraction with dichloromethane. Purification by flash chromatography (silica, ethyl acetate/n-heptane, 1:9) gave the title compound in 89% yleld.

Workup

customVolatiles were removed in vacuo
additionthe residue treated with a water/dichloromethane mixture
extractionfollowed by extraction with dichloromethane
customPurification by flash chromatography (silica, ethyl acetate/n-heptane, 1:9)

Sources & evidence

ORD record: ord-e11ea5b19115474eb1e369b55912a579
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07592363B2

Reaction notes

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