Boron Trichloride → HCID 136393282, compound

HRID 735443Notes

Reaction equation

HRID 735443 reaction equation
[CH3:1][C:2]1[CH:30]=[C:29]([CH3:31])[CH:28]=[CH:27][C:3]=1[CH2:4][N:5]1[C:13]([C:14]2[CH:19]=[CH:18][C:17]([O:20]C)=[CH:16][C:15]=2[CH3:22])=[C:12]2[C:7]([C:8]([C:23]([F:26])([F:25])[F:24])=[CH:9][CH:10]=[CH:11]2)=[N:6]1.B(Cl)(Cl)Cl>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.C(Cl)Cl>[CH3:1][C:2]1[CH:30]=[C:29]([CH3:31])[CH:28]=[CH:27][C:3]=1[CH2:4][N:5]1[C:13]([C:14]2[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][C:15]=2[CH3:22])=[C:12]2[C:7]([C:8]([C:23]([F:26])([F:25])[F:24])=[CH:9][CH:10]=[CH:11]2)=[N:6]1

Participants

5

Reactant 2

HCID 25135Boron TrichlorideHCID 67021040HCID 67021040, compound

Product 1

HCID 136393282HCID 136393282, compoundYield 69.6%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A solution of 2-(2,4-Dimethylbenzyl)-3-(4-methoxy-2-methylphenyl)-7-trifluoromethyl-2H-indazole (0.27 g, 0.63 mmol) and tetrabutylammonium iodide (0.7 g, 1.9 mmol) in 10 mL of CH2Cl2 was cooled to −78° C. and treated with boron trichloride 1M in CH2Cl2 (1.9 mL, 1.9 mmol). The reaction mixture was allowed to warm to ambient temperature. The reaction mixture was partitioned with 1N HCl and the organic phase was concentrated in vacuo. The residue was purified by flash chromatography to give 0.18 g of title compound as a white solid.

Workup

  1. customThe reaction mixture was partitioned with 1N HCl
  2. concentrationthe organic phase was concentrated in vacuo
  3. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-7e25a475339e4adba5a4a2eec6a23cff
Source dataset
uspto-grants-2009_09
Patent number
US07592363B2

Reaction notes

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