Benzoyl chloride → HCID 86603026, compound

HRID 735464Notes

Reaction equation

HRID 735464 reaction equation
[N:1]1([C:7]2[CH:12]=[CH:11][C:10]([C:13]3[N:14]([CH2:26][C:27]4[C:32]([F:33])=[CH:31][C:30]([F:34])=[CH:29][C:28]=4[F:35])[N:15]=[C:16]4[C:21]=3[CH:20]=[CH:19][CH:18]=[C:17]4[C:22]([F:25])([F:24])[F:23])=[CH:9][CH:8]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[C:36](Cl)(=[O:43])[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1.C(N(C(C)C)CC)(C)C.C1COCC1>C(OCC)(=O)C.O>[C:36]([N:4]1[CH2:5][CH2:6][N:1]([C:7]2[CH:8]=[CH:9][C:10]([C:13]3[N:14]([CH2:26][C:27]4[C:28]([F:35])=[CH:29][C:30]([F:34])=[CH:31][C:32]=4[F:33])[N:15]=[C:16]4[C:21]=3[CH:20]=[CH:19][CH:18]=[C:17]4[C:22]([F:23])([F:24])[F:25])=[CH:11][CH:12]=2)[CH2:2][CH2:3]1)(=[O:43])[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1

Participants

7

Reactant 4

HCID 7412Benzoyl chlorideHCID 8028TetrahydrofuranHCID 81531DiisopropylethylamineHCID 86603027HCID 86603027, compound

Product 1

HCID 86603026HCID 86603026, compoundYield 50.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

Combined in a vial were 3-(4-piperazin-1-ylphenyl)-2-(2,4,6-trifluorobenzyl)-7-(trifluoromethyl)-2H-indazole (0.10 g, 0.2 mmol), benzoyl chloride (0.030 g, 0.22 mmol), and diisopropylethylamine (0.2 mL) and THF (2 mL), which were stirred overnight at room temperature. Then the reaction mixture was diluted with ethyl acetate and water, and the organics washed with water and brine, then dried over magnesium sulfate. The crude product was purified by flash chromatography (silica 60, 5% EtOAc/CH2Cl2) to provide the title compound (0.06 g, 50%).

Workup

  1. washthe organics washed with water and brine
  2. dry with materialdried over magnesium sulfate
  3. customThe crude product was purified by flash chromatography (silica 60, 5% EtOAc/CH2Cl2)

Sources & evidence

ORD record
ord-52de1a143f0040e49d31d7afba4cc7d4
Source dataset
uspto-grants-2009_09
Patent number
US07592363B2

Reaction notes

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