HCID 89718115, compound → HCID 178451747, compound

HRID 1518965Notes

Reaction equation

HRID 1518965 reaction equation
C([O:8][C:9]1[N:14]=[C:13]([C:15]2[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:17][CH:16]=2)[CH:12]=[CH:11][CH:10]=1)C1C=CC=CC=1>CO.[Pd]>[OH:8][C:9]1[N:14]=[C:13]([CH:15]2[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:17][CH2:16]2)[CH:12]=[CH:11][CH:10]=1

Participants

4

Reactant 1

HCID 89718115HCID 89718115, compound

Product 1

HCID 178451747HCID 178451747, compoundYield 60.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 887MethanolSolvent

Procedure

Add Pd/C (5 wt/wt %, 0.26 g, 0.12 mmol) to a solution of tert-butyl 4-(6-(benzyloxy)pyridin-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate (2.6 g; 7.1 mmol) in methanol (20 mL) add Pd/C (5 wt/wt %, 0.26 g, 0.12 mmol) and stir overnight under a hydrogen balloon. Filter and concentrate under vacuum to give the crude product. Purify with normal phase silica gel flash column chromatography, using a gradient of 0-20% MeOH in DCM to give the title product as a white solid (1.2 g, 615). MS (m/z): 223 (M-t-Bu+1).

Workup

  1. filtrationFilter
  2. concentrationconcentrate under vacuum
  3. customto give the crude product
  4. customPurify with normal phase silica gel flash column chromatography

Sources & evidence

ORD record
ord-6986412a982c4ed089cf20a453964ffc
Source dataset
uspto-grants-2015_07
Patent number
US09073856B2

Reaction notes

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