HCID 69052796, compound → HCID 57832818, compound

HRID 729612Notes

Reaction equation

HRID 729612 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]([N:10]1[CH2:15][CH2:14][CH:13]([O:16][C:17]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[C:20]([N+:27]([O-])=O)=[CH:19][N:18]=2)[CH2:12][CH2:11]1)=[O:9]>[Pd].CO>[NH2:27][C:20]1[C:21]2[C:26](=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:17]([O:16][CH:13]2[CH2:14][CH2:15][N:10]([C:8]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[F:1])=[O:9])[CH2:11][CH2:12]2)=[N:18][CH:19]=1

Participants

4

Reactant 1

HCID 69052796HCID 69052796, compound

Product 1

HCID 57832818HCID 57832818, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Stir a suspension of (2-fluoro-phenyl)-[4-(4-nitro-isoquinoline-1-yloxy)-piperidin-1-yl]-methanone (5.85 g, 14.8 mmol) and palladium on carbon (10%, 2.9 g) in methanol (250 mL) under hydrogen overnight. Remove the catalyst by filtration. Concentrate the filtrate to yield a pale yellow solid (4.7 g, 87% yield, ES+ (m/z) 366.3 [M+H]).

Workup

  1. customRemove the catalyst
  2. filtrationby filtration
  3. concentrationConcentrate the filtrate
  4. customto yield a pale yellow solid (4.7 g, 87% yield, ES+ (m/z) 366.3 [M+H])

Sources & evidence

ORD record
ord-d14feb8b64264659b397647fe87296ff
Source dataset
uspto-grants-2009_09
Patent number
US07582638B2

Reaction notes

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