HCID 90402594, compound → HCID 90403327, compound

HRID 1049271Notes

Reaction equation

HRID 1049271 reaction equation
[C:1]([O:7][CH2:8][N:9]1[CH:13]=[C:12]([C:14]2[CH:19]=[C:18]([O:20][C:21]3[C:22]([CH3:30])=[N:23][C:24]([N+:27]([O-])=O)=[CH:25][CH:26]=3)[CH:17]=[CH:16][N:15]=2)[N:11]=[N:10]1)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3]>CCOC(C)=O.[Pd]>[C:1]([O:7][CH2:8][N:9]1[CH:13]=[C:12]([C:14]2[CH:19]=[C:18]([O:20][C:21]3[C:22]([CH3:30])=[N:23][C:24]([NH2:27])=[CH:25][CH:26]=3)[CH:17]=[CH:16][N:15]=2)[N:11]=[N:10]1)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3]

Participants

4

Reactant 1

HCID 90402594HCID 90402594, compound

Product 1

HCID 90403327HCID 90403327, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of (4-(4-((2-methyl-6-nitropyridin-3-yl)oxy)pyridin-2-yl)-1H-1,2,3-triazol-1-yl)methyl pivalate (0.27 g, 0.655 mmol) in EtOAc (5 mL) was treated with 10% Pd/C (50% wet, 0.070 g, 0.066 mmol) and the mixture was stirred under hydrogen (1 atm) at RT for 24 h. The mixture was filtered through diatomaceous earth and the filter cake was washed with EtOAc. The combined filtrates were evaporated to dryness to give (4-(4-((6-amino-2-methylpyridin-3-yl)oxy)pyridin-2-yl)-1H-1,2,3-triazol-1-yl)methyl pivalate (0.24 g, 96%) as colorless foam. 1H NMR (400 MHz, DMSO-d6): δ 8.67 (s, 1H), 8.45 (d, J=5.7 Hz, 1H), 7.35 (d, J=2.5 Hz, 1H), 7.23 (d, J=8.7 Hz, 1H), 6.86 (dd, J=5.7, 2.6 Hz, 1H), 6.38-6.35 (m, 3H); 5.99 (s, 2H), 2.06 (s, 3H), 1.11 (s, 9H); MS (ESI) m/z: 383.2 (M+H+).

Workup

  1. filtrationThe mixture was filtered through diatomaceous earth
  2. washthe filter cake was washed with EtOAc
  3. customThe combined filtrates were evaporated to dryness

Sources & evidence

ORD record
ord-f006660dfb2a4d0ea34424e2d22e0774
Source dataset
uspto-grants-2016_07
Patent number
US09382228B2

Reaction notes

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