HCID 21877263, compound → HCID 21877604, compound

HRID 724371Notes

Reaction equation

HRID 724371 reaction equation
[CH:1](/[C:9]1[C:17]2[CH2:16][CH2:15][C:14]([O:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[CH:13][C:12]=2[NH:11][N:10]=1)=[CH:2]\[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1>C1C2C(=CC=CC=2)CCC1.[Pd]>[CH:1](/[C:9]1[C:17]2[C:12](=[CH:13][C:14]([O:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[CH:15][CH:16]=2)[NH:11][N:10]=1)=[CH:2]\[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 1

HCID 21877263HCID 21877263, compound

Product 1

HCID 21877604HCID 21877604, compoundYield 55%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8404TetralinSolvent

Conditions

Temperature
155 °C

Procedure

A suspension of 3-(E-styryl)-6-phenoxy-4,5-dihydro-1H-indazole (200 mg. 0.64 mmol) and 5% Pd/C (200 mg) in 10 mL of tetralin was heated at 155° C. for 18 h. The catalyst was removed by filtering the hot solution and washed with THF, EtOAc and MeOH. The filtrate was concentrated under reduced pressure and the residue was chromatographed on silica gel eluting hexanes/EtOAc (2:1) to provide 3-(E-styryl)-6-phenoxy-1H-indazole as an off-white solid (110 mg, 55%). 1H NMR (DMSO-d6) δ 6.96 (s, 2H), 7.10 (d, 2H, J=7.7 Hz), 7.20 (t, 1H, J=7.1 Hz), 7.30 (t, 1H, J=7.1 Hz), 7.44 (m, 6H), 7.71 (d, 2H, J=7.5 Hz), 8.20 (d, 1H, J=9.2 Hz), 12.90 (s, 1H). Anal. Calc. for C21H16N2O.0.1H2O: C, 80.28; H, 5.20; N, 8.92. Found: C, 80.20; H, 5.21; N, 8.93.

Workup

  1. customThe catalyst was removed
  2. filtrationby filtering the hot solution
  3. washwashed with THF, EtOAc and MeOH
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customthe residue was chromatographed on silica gel
  6. washeluting hexanes/EtOAc (2:1)

Sources & evidence

ORD record
ord-2ae6df201b0045b284e4cad8485250a2
Source dataset
uspto-grants-2006_11
Patent number
US07141587B2

Reaction notes

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