HCID 12169650, compound → 1H-Indazole

HRID 2181556Notes

Reaction equation

HRID 2181556 reaction equation
C([C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5](COCC[Si](C)(C)C)[N:4]=1)=C.FC1C(OC=O)=C(F)C(F)=C(F)C=1F>C(Cl)Cl.CCOC(C)=O>[NH:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH:3]=[N:4]1

Participants

5

Reactant 2

HCID 12169650HCID 12169650, compoundHCID 86759726HCID 86759726, compound

Product 1

HCID 92211H-IndazoleYield 190.5%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

6-(3-Benzamidobenzoyl)-3-E-2-aminophenyl)ethenyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-indazole (0.17, 0.28 mmol) was dissolved in 3 mL of methylene chloride. To this was added formic acid pentafluorophenyl ester (0.12 g, 0.56 mmol) dropwise. After 3 h, the reaction mixture was diluted with 40 mL of EtOAc and was washed with 50/50 NaHCO3 (2×30 mL) and the organic layer was filtered through a silica plug. The residue was purified by radial chromatography through silica eluting with hexane:EtOAc/CH2Cl2 (1:1:1) which afforded 6-(3-benzamidobenzoyl)-3-E-(2-formamidophenyl)ethenyl]-(2-trimethylsilanyl)-ethoxymethyl)-1H-indazole as a clear oil (63 mg, 40%). 1H NMR (CDCl3) δ 8.48-8.36 (m, 1H), 8.20-7.84 (m, 4H), 7.61-7.52 (m, 5H), 7.41-7.32 (m, 4H), 7.26-7.01 (m, 4H), 6.82 (t, 1H, J=14.2 Hz), 3.48-3.23 (m, 2H), 0.95-0.87 (m, 2H), −0.05 (s, 9H).

Workup

  1. washwas washed with 50/50 NaHCO3 (2×30 mL)
  2. filtrationthe organic layer was filtered through a silica plug
  3. customThe residue was purified by radial chromatography through silica eluting with hexane

Sources & evidence

ORD record
ord-2d499e9c81484bafa40df2987a4c2e2c
Source dataset
uspto-grants-2005_05
Patent number
US06891044B2

Reaction notes

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