HCID 90403112, compound → HCID 90403028, compound

HRID 1049251Notes

Reaction equation

HRID 1049251 reaction equation
[CH3:1][C:2]1[S:3][C:4]([C:7]2[CH:12]=[C:11]([O:13][C:14]3[C:15]([CH3:23])=[N:16][C:17]([N+:20]([O-])=O)=[CH:18][CH:19]=3)[CH:10]=[CH:9][N:8]=2)=[CH:5][N:6]=1>CO.[Pd]>[CH3:23][C:15]1[N:16]=[C:17]([NH2:20])[CH:18]=[CH:19][C:14]=1[O:13][C:11]1[CH:10]=[CH:9][N:8]=[C:7]([C:4]2[S:3][C:2]([CH3:1])=[N:6][CH:5]=2)[CH:12]=1

Participants

4

Reactant 1

HCID 90403112HCID 90403112, compound

Product 1

HCID 90403028HCID 90403028, compoundYield 70.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 2-methyl-5-(4-((2-methyl-6-nitropyridin-3-yl)oxy)pyridin-2-yl)thiazole (0.094 g, 0.286 mmol) in MeOH (30 mL) was flushed with Ar, treated with 10% Pd/C (50% wet, 0.305 g, 0.286 mmol) and hydrogenated (1 atm) overnight. The solids were removed via filtration through diatomaceous earth, washed well with MeOH and the filtrate was concentrated to dryness to afford 6-methyl-5-((2-(2-methylthiazol-5-yl)pyridin-4-yl)oxy)pyridin-2-amine (60 mg, 70%). 1H NMR (400 MHz, DMSO-d6): δ 8.34 (d, J=5.8 Hz, 1H), 8.28 (s, 1H), 7.49 (d, J=2.4 Hz, 1H), 7.19 (d, J=8.7 Hz, 1H), 6.58 (dd, J=5.8, 2.4 Hz, 1H), 6.34 (d, J=8.7 Hz, 1H), 5.96 (s, 2H), 2.65 (s, 3H), 2.07 (s, 3H); MS (ESI) m/z: 299.1 (M+H+).

Workup

  1. customThe solids were removed via filtration through diatomaceous earth
  2. washwashed well with MeOH
  3. concentrationthe filtrate was concentrated to dryness

Sources & evidence

ORD record
ord-8bce42a64dd64ef79f46fcbef710de2d
Source dataset
uspto-grants-2016_07
Patent number
US09382228B2

Reaction notes

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