HCID 86722338, compound → HCID 86722339, compound

HRID 718757Notes

Reaction equation

HRID 718757 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13]4=[C:14]([CH2:17][CH2:18][CH2:19][C:20](=[O:29])/[C:21]/4=[CH:22]/[C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=4)[CH:15]=3)[CH:10]=[N:9]2)=[CH:4][CH:3]=1>C1(C)C=CC=CC=1.[OH-].[OH-].[Pd+2]>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13]4[CH:21]([CH2:22][C:23]5[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=5)[C:20](=[O:29])[CH2:19][CH2:18][CH2:17][C:14]=4[CH:15]=3)[CH:10]=[N:9]2)=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 86722338HCID 86722338, compound

Product 1

HCID 86722339HCID 86722339, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 1140TolueneSolvent

Procedure

A solution of (E)-1-(4-fluorophenyl)-5-(pyridin-2-ylmethylene)-5,7,8,9-tetrahydrocyclohepta[f]indazol-6(1H)-one (0.519 g, 1.354 mmol) in toluene (25 mL) containing 20% Pd(OH)2 (0.090 g, 0.128 mmol) was evacuated and placed under hydrogen. The mixture was stirred under an atmosphere of hydrogen provided via a balloon at rt for about 11 h then the catalyst was removed by filtration through Celite®. The filtrate was concentrated under reduced pressure to yield 1-(4-fluorophenyl)-5-(pyridin-2-ylmethyl)-5,7,8,9-tetrahydrocyclohepta[f]indazol-6(1H)-one (7, R1=4-Fluorophenyl, R2=Pyridin-2-ylmethyl) (0.52 g, 100%); LC/MS, method 3, Rt=2.06 min, MS m/z 386 (M+H)+. 1H NMR (400 MHz, DMSO) δ 8.48-8.46 (m, 1H), 8.27 (d, J=0.8 Hz, 1H), 7.84-7.75 (m, 2H), 7.72-7.63 (m, 3H), 7.47-7.38 (m, 2H), 7.36 (d, J=7.8 Hz, 1H), 7.21-7.17 (m, 1H), 4.95-4.92 (m, 1H), 3.88-3.81 (m, 1H), 3.44-3.36 (m, 1H), 3.34-3.27 (m, 1H), 3.12-3.06 (m, 1H), 2.98-2.90 (m, 1H), 2.47-2.40 (m, 1H), 2.27-2.17 (m, 1H), 1.60-1.57 (m, 1H).

Workup

  1. customwas evacuated
  2. customprovided via a balloon at rt for about 11 h
  3. customthe catalyst was removed by filtration through Celite®
  4. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-3377c5e50ff1422db36261038c286fea
Source dataset
uspto-grants-2015_11
Patent number
US09193744B2

Reaction notes

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