HCID 19595150, compound → HCID 19595269, compound

HRID 612484Notes

Reaction equation

HRID 612484 reaction equation
C([O:8][C:9]1[C:10]([O:27][CH3:28])=[CH:11][C:12]([Br:26])=[C:13]2[C:18]=1[CH2:17][N:16]([NH:19][C:20]1[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=1)[CH2:15][CH2:14]2)C1C=CC=CC=1>C(O)C.[Pd]>[BrH:26].[CH3:28][O:27][C:10]1[C:9]([OH:8])=[C:18]2[C:13]([CH2:14][CH2:15][N:16]([NH:19][C:20]3[CH:21]=[CH:22][N:23]=[CH:24][CH:25]=3)[CH2:17]2)=[CH:12][CH:11]=1

Participants

4

Reactant 1

HCID 19595150HCID 19595150, compound

Product 1

HCID 19595269HCID 19595269, compoundYield 94.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

(8-Benzyloxy-5-bromo-3,4-dihydro-7-methoxy-1H-isoquinolin-2-yl)-4-pyridinylamine) (11 g) was dissolved in ethanol (250 ml) and slowly added to 5% palladium-on-carbon (2.2 g). The mixture was hydrogenated at 55 psi overnight in a parr shaker at ambient temperature. The reaction mixture was filtered through a pad of Celite, and the pad was washed well with methanol. The filtrate was concentrated, and the precipitate was collected and dried to give 8.3 g, 94.6% of product, mp 235-236° C.

Workup

  1. customwas hydrogenated at 55 psi overnight in a parr shaker at ambient temperature
  2. filtrationThe reaction mixture was filtered through a pad of Celite
  3. washthe pad was washed well with methanol
  4. concentrationThe filtrate was concentrated
  5. customthe precipitate was collected
  6. customdried

Sources & evidence

ORD record
ord-f074aad0e36349f08b50290662fc4f2b
Source dataset
uspto-grants-1999_12
Patent number
US06004977

Reaction notes

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