HCID 59418660, compound → HCID 59418696, compound

HRID 1641093Notes

Reaction equation

HRID 1641093 reaction equation
C([O:8][C:9]1[CH:10]=[CH:11][C:12]([C:19]2[CH:28]=[C:27]3[C:22]([CH2:23][CH2:24][CH2:25][N:26]3[C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])=[CH:21][CH:20]=2)=[N:13][C:14]=1[C:15]([O:17][CH3:18])=[O:16])C1C=CC=CC=1>CCOC(C)=O.CCO.C(O)(=O)C.[Pd]>[OH:8][C:9]1[CH:10]=[CH:11][C:12]([C:19]2[CH:28]=[C:27]3[C:22]([CH2:23][CH2:24][CH2:25][N:26]3[C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])=[CH:21][CH:20]=2)=[N:13][C:14]=1[C:15]([O:17][CH3:18])=[O:16]

Participants

6

Reactant 1

HCID 59418660HCID 59418660, compound

Product 1

HCID 59418696HCID 59418696, compound

Reagents, catalysts & solvents 4

HCID 176Acetic AcidCatalystHCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of tert-butyl 7-(5-(benzyloxy)-6-(methoxycarbonyl)pyridin-2-yl)-3,4-dihydroquinoline-1(2H)-carboxylate (29C) (2.72 g, 5.74 mmol) in EtOAc (80 mL) and EtOH (80 mL) and glacial acetic acid (˜30 drops) was added 10% Pd—C (420 mg). The reaction mixture was stirred under an atmosphere of hydrogen for 24 hrs, filtered through a bed of Celite, and concentrated to provide the desired product tert-butyl 7-(5-hydroxy-6-(methoxycarbonyl)pyridin-2-yl)-3,4-dihydroquinoline-1(2H)-carboxylate (29D): 1H NMR (300 MHz, CDCl3) δ 10.67 (1H, s), 8.30 (1H, d), 7.86 (1H, d), 7.56 (1H, dd), 7.42 (1H, d), 7.15 (1H, d), 4.05 (3H, s), 3.74 (2H, m), 2.80 (2H, t), 1.95 (2H, m), 1.56 (9H, s).

Workup

  1. filtrationfiltered through a bed of Celite
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-be403951d59b44958b7c417b4dafc8fa
Source dataset
uspto-grants-2012_02
Patent number
US08114893B2

Reaction notes

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