HCID 86722474, compound → HCID 86722475, compound

HRID 718860Notes

Reaction equation

HRID 718860 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]2/[C:9](=[CH:15]\[C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=3)/[C:10](=[O:14])[CH2:11][CH2:12][CH2:13][C:5]=2[CH:4]=1>C1(C)C=CC=CC=1.[OH-].[OH-].[Pd+2]>[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]2[CH:9]([CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=3)[C:10](=[O:14])[CH2:11][CH2:12][CH2:13][C:5]=2[CH:4]=1

Participants

4

Reactant 1

HCID 86722474HCID 86722474, compound

Product 1

HCID 86722475HCID 86722475, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 1140TolueneSolvent

Procedure

(E)-3-Methoxy-9-(pyridin-2-ylmethylene)-6,7-dihydro-5H-cyclohepta[c]pyridin-8 (9H)-one (127, R5=Pyridin-2-yl) (36.15 g, 129 mmol) in toluene (800 mL) with 20 wt % (wet) palladium hydroxide on carbon (4.53 g, 6.45 mmol) was stirred under a hydrogen filled balloon for about 7 h. The catalyst was removed by filtration through a pad of Celite® then the pad was washed with toluene (250 mL). The filtrate was concentrated under reduced pressure then the material was purified on silica gel (330 g) using 100% EtOAc. Product fractions were combined and concentrated under reduced pressure to yield 3-methoxy-9-(pyridin-2-ylmethyl)-6,7-dihydro-5H-cyclohepta[c]pyridin-8(9H)-one (128, R2=Pyridin-2-ylmethyl) (26.64 g, 73%); LC/MS, method 3, Rt=1.14 min, MS m/z 283 (M+H)+. 1H NMR (400 MHz, DMSO) δ 8.48-8.43 (m, 1H), 7.79 (s, 1H), 7.71-7.64 (m, 1H), 7.29 (d, J=7.8 Hz, 1H), 7.20-7.17 (m, 1H), 6.68 (s, 1H), 4.69-4.60 (m, 1H), 3.78 (s, 3H), 3.74-3.68 (m, 1H), 3.25-3.06 (m, 2H), 2.92-2.78 (m, 2H), 2.49-2.43 (m, 1H), 2.15-2.01 (m, 1H), 1.75-1.57 (m, 1H).

Workup

  1. customThe catalyst was removed by filtration through a pad of Celite®
  2. washthe pad was washed with toluene (250 mL)
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customthe material was purified on silica gel (330 g)
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6847a73a3e224adfa9a29c67ba3c1ede
Source dataset
uspto-grants-2015_11
Patent number
US09193744B2

Reaction notes

Loading…