2-(2-benzyloxy-pyridin-3-yl)-4-tert-butyl-5-methoxy-N-methyl-benzamide → 4-tert-Butyl-5-methoxy-N-methyl-2-(2-oxo-1,2-dihydro-pyridin-3-yl)-benzamide

HRID 1517532Notes

Reaction equation

HRID 1517532 reaction equation
C([O:8][C:9]1[C:14]([C:15]2[CH:24]=[C:23]([C:25]([CH3:28])([CH3:27])[CH3:26])[C:22]([O:29][CH3:30])=[CH:21][C:16]=2[C:17]([NH:19][CH3:20])=[O:18])=[CH:13][CH:12]=[CH:11][N:10]=1)C1C=CC=CC=1>CO.[Pd]>[C:25]([C:23]1[C:22]([O:29][CH3:30])=[CH:21][C:16]([C:17]([NH:19][CH3:20])=[O:18])=[C:15]([C:14]2[C:9](=[O:8])[NH:10][CH:11]=[CH:12][CH:13]=2)[CH:24]=1)([CH3:28])([CH3:26])[CH3:27]

Participants

4

Reactant 1

HCID 685919252-(2-benzyloxy-pyridin-3-yl)-4-tert-butyl-5-methoxy-N-methyl-benzamide

Product 1

HCID 461951884-tert-Butyl-5-methoxy-N-methyl-2-(2-oxo-1,2-dihydro-pyridin-3-yl)-benzamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

step 3—A mixture of 62 (95 mg) and 10% Pd/C (10 mg) in MeOH (5 mL) at RT was stirred under 1 atmosphere of H2 for 0.5 h. The catalyst was filtered off, and the filtrate was concentrated. The crude residue was purified on a preparative SiO2 TLC plate developed with 8% MeOH/DCM to afford 41 mg of I-9 as a white solid.

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated
  3. customThe crude residue was purified on a preparative SiO2 TLC plate
  4. customto afford 41 mg of I-9 as a white solid

Sources & evidence

ORD record
ord-f825fa547dc14b1784bd93f02ba80a52
Source dataset
uspto-grants-2012_07
Patent number
US08232271B2

Reaction notes

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