1-(Bromomethyl)-3-(trifluoromethyl)benzene → 3-iodo-4-nitro-1-(3-(trifluoromethyl)benzyl)-1H-indazole
Reaction equation
[I:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[N+:11]([O-:13])=[O:12])[NH:4][N:3]=1.Br[CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:25])([F:24])[F:23])[CH:17]=1.C(N=C(N(C)C)N(C)C)(C)(C)C>CC#N>[I:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[N+:11]([O-:13])=[O:12])[N:4]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:23])([F:24])[F:25])[CH:17]=2)[N:3]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a slurry of 3-iodo-4-nitro-1H-indazole (0.410 g, 1.42 mmol) and CH3CN (7.0 mL) was added 1-(bromomethyl)-3-(trifluoromethyl)benzene (0.261 mL, 1.70 mmol) and the solution was cooled to 0° C. 2-tert-Butyl-1,1,3,3-tetramethylguanidine (0.372 mL, 1.84 mmol) was added and the mixture was gradually warmed to ambient temperature where it stirred for 2 hours. The mixture was concentrated and diluted with saturated aqueous NH4Cl (20 mL) and EtOAc (75 mL). The layers were mixed and separated and the organic phase was washed with brine, dried over Na2SO4, filtered and concentrated. The crude product was passed through a silica gel plug eluting with 20% EtOAc/hexane to provide 0.542 g (85%) of the product as dark yellow/orange oil.
Workup
- temperaturethe mixture was gradually warmed to ambient temperature where it
- concentrationThe mixture was concentrated
- additiondiluted with saturated aqueous NH4Cl (20 mL) and EtOAc (75 mL)
- additionThe layers were mixed
- customseparated
- washthe organic phase was washed with brine
- dry with materialdried over Na2SO4
- filtrationfiltered
- concentrationconcentrated
- washeluting with 20% EtOAc/hexane
Sources & evidence
- ORD record
- ord-2cf1b510d7344e71b45a69e87c0f7f47
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09174981B2
Reaction notes
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