2-(2-Benzyloxypyridin-3-yl)-4-tert-butyl-5-methoxybenzoic acid ethyl ester → 4-tert-Butyl-5-methoxy-2-(2-oxo-1,2-dihydro-pyridin-3-yl)-benzoic acid ethyl ester

HRID 1517540Notes

Reaction equation

HRID 1517540 reaction equation
[CH2:1]([O:3][C:4](=[O:31])[C:5]1[CH:10]=[C:9]([O:11][CH3:12])[C:8]([C:13]([CH3:16])([CH3:15])[CH3:14])=[CH:7][C:6]=1[C:17]1[C:18]([O:23]CC2C=CC=CC=2)=[N:19][CH:20]=[CH:21][CH:22]=1)[CH3:2]>CO.C1COCC1.[OH-].[OH-].[Pd+2]>[CH2:1]([O:3][C:4](=[O:31])[C:5]1[CH:10]=[C:9]([O:11][CH3:12])[C:8]([C:13]([CH3:16])([CH3:15])[CH3:14])=[CH:7][C:6]=1[C:17]1[C:18](=[O:23])[NH:19][CH:20]=[CH:21][CH:22]=1)[CH3:2]

Participants

5

Reactant 1

HCID 673750432-(2-Benzyloxypyridin-3-yl)-4-tert-butyl-5-methoxybenzoic acid ethyl ester

Product 1

HCID 461960444-tert-Butyl-5-methoxy-2-(2-oxo-1,2-dihydro-pyridin-3-yl)-benzoic acid ethyl ester

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

step 2—To a solution of 78 (109 mg, 0.26 mmol) in MeOH (7 mL) and THF (1 mL) was added 20% Pd(OH)2/C (wet, 20 mg). The reaction mixture was stirred under an atmosphere of hydrogen (balloon) for 2 h then filtered through a pad of CELITE, rinsing with EtOAc. The filtrate was concentrated under reduced pressure to afford 79 mg (93%) of I-54 as an off-white solid: MS=330 [M+H]+.

Workup

  1. filtrationthen filtered through a pad of CELITE
  2. washrinsing with EtOAc
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customto afford 79 mg (93%) of I-54 as an off-white solid

Sources & evidence

ORD record
ord-b647851804194a9badfffa3c25785346
Source dataset
uspto-grants-2012_07
Patent number
US08232271B2

Reaction notes

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