HCID 86722324, compound → HCID 86722326, compound

HRID 718750Notes

Reaction equation

HRID 718750 reaction equation
[CH:1](=[C:3]1/[C:4](=[O:24])[CH2:5][CH2:6][CH2:7][C:8]2[CH:16]=[C:15]3[C:11]([CH:12]=[N:13][N:14]3[C:17]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=3)=[CH:10][C:9]/1=2)\[CH3:2]>C1(C)C=CC=CC=1.[OH-].[OH-].[Pd+2]>[CH2:1]([CH:3]1[C:9]2[CH:10]=[C:11]3[C:15](=[CH:16][C:8]=2[CH2:7][CH2:6][CH2:5][C:4]1=[O:24])[N:14]([C:17]1[CH:18]=[CH:19][C:20]([F:23])=[CH:21][CH:22]=1)[N:13]=[CH:12]3)[CH3:2]

Participants

4

Reactant 1

HCID 86722324HCID 86722324, compound

Product 1

HCID 86722326HCID 86722326, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 1140TolueneSolvent

Procedure

A solution of (E)-5-ethylidene-1-(4-fluorophenyl)-5,7,8,9-tetrahydrocyclohepta[f]indazol-6(1H)-one (3.27 g, 10.21 mmol) in toluene (75 mL) containing 20% Pd(OH)2 on carbon (0.300 g, 0.427 mmol) was evacuated and placed under hydrogen. The reaction was shaken under about 50 psi of hydrogen for about 1 h, then the catalyst was removed by filtration through Celite® and the filtrate concentrated under reduced pressure to yield 5-ethyl-1-(4-fluorophenyl)-5,7,8,9-tetrahydrocyclohepta[f]indazol-6(1H)-one (7, R1=4-Fluorophenyl, R2=Ethyl) (3.25 g, 99%); LC/MS, method 3, Rt=2.69 min, MS m/z 323 (M+H)+. 1H NMR (400 MHz, DMSO) δ 8.29 (d, J=0.9 Hz, 1H), 7.84-7.77 (m, 2H), 7.65 (s, 1H), 7.62 (s, 1H), 7.47-7.38 (m, 2H), 4.08 (t, J=7.0 Hz, 1H), 3.33-3.24 (m, 1H), 3.03-2.97 (m, 1H), 2.79-2.72 (m, 1H), 2.43-2.35 (m, 1H), 2.33-2.05 (m, 2H), 1.83-1.59 (m, 2H), 0.90 (t, J=7.3 Hz, 3H).

Workup

  1. customwas evacuated
  2. customthe catalyst was removed by filtration through Celite®
  3. concentrationthe filtrate concentrated under reduced pressure

Sources & evidence

ORD record
ord-53bf0e78c0f34b6bb60460b86506fdd3
Source dataset
uspto-grants-2015_11
Patent number
US09193744B2

Reaction notes

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