HCID 90403039, compound → HCID 90403388, compound

HRID 1049351Notes

Reaction equation

HRID 1049351 reaction equation
[N+:1]([C:4]1[N:9]=[CH:8][C:7]([O:10][C:11]2[CH:16]=[CH:15][N:14]=[C:13]([C:17]3[CH:18]=[N:19][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:21][CH:22]=3)[CH:12]=2)=[CH:6][CH:5]=1)([O-])=O>CO.[Pd]>[F:26][C:23]([F:24])([F:25])[C:20]1[N:19]=[CH:18][C:17]([C:13]2[CH:12]=[C:11]([O:10][C:7]3[CH:6]=[CH:5][C:4]([NH2:1])=[N:9][CH:8]=3)[CH:16]=[CH:15][N:14]=2)=[CH:22][CH:21]=1

Participants

4

Reactant 1

HCID 90403039HCID 90403039, compound

Product 1

HCID 90403388HCID 90403388, compoundYield 39%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 4-((6-nitropyridin-3-yl)oxy)-6′-(trifluoromethyl)-2,3′-bipyridine (0.177 g, 0.489 mmol) in MeOH (10 mL) was treated with 10% Pd/C (50% wet, 0.052 g, 0.049 mmol) and hydrogenated (1 atm) for 5 h. The solid was removed via filtration through diatomaceous earth, and the filtrate was concentrated to dryness and purified via silica gel chromatography (MeOH/EtOAc) to afford 5-((6′-(trifluoromethyl)-[2,3′-bipyridin]-4-yl)oxy)pyridin-2-amine (63 mg, 39%). 1H NMR (400 MHz, DMSO-d6): δ 9.39 (s, 1H), 8.66 (d, J=8.4 Hz, 1H), 8.57 (d, J=5.7 Hz, 1H), 8.00 (d, J=8.2 Hz, 1H), 7.85 (d, J=2.9 Hz, 1H), 7.75 (d, J=2.4 Hz, 1H), 7.33 (dd, J=8.9, 3.0 Hz, 1H), 6.86 (dd, J=5.7, 2.4 Hz, 1H), 6.53 (d, J=8.9 Hz, 1H), 6.05 (s, 2H); MS (ESI) m/z: 333.1 (M+H+).

Workup

  1. customThe solid was removed via filtration through diatomaceous earth
  2. concentrationthe filtrate was concentrated to dryness
  3. custompurified via silica gel chromatography (MeOH/EtOAc)

Sources & evidence

ORD record
ord-974056b65de34e448b5ca277c1d97ac6
Source dataset
uspto-grants-2016_07
Patent number
US09382228B2

Reaction notes

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