Acetonitrile → 2-(2-(2-Picolyl)aminoanilin-5-yl)benzoxazole

HRID 74251Notes

Reaction equation

HRID 74251 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]3[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=3[N:12]=2)=[CH:4][C:3]=1[N+:17]([O-])=O.C(#N)C.[N:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[CH2:29][NH2:30].[H][H]>[C].[Pd].O>[N:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[CH2:29][NH:30][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]3[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=3[N:12]=2)=[CH:4][C:3]=1[NH2:17]

Participants

7

Reactant 4

HCID 6342AcetonitrileHCID 195092-PyridinemethanamineHCID 219909702-(4-Fluoro-3-nitrophenyl)benzoxazoleHCID 178418361HCID 178418361, compound

Product 1

HCID 674984162-(2-(2-Picolyl)aminoanilin-5-yl)benzoxazoleYield 79.9%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 962WaterSolvent

Procedure

2-(4-Fluoro-3-nitrophenyl)benzoxazole (see Working Example 15-2) (500 mg, 1.9 mmol) was added to an acetonitrile (5 mL) suspension containing 2-picolylamine (520 mg, 4.8 mmol), and this was heated to reflux for 2.5 hours. After the reaction was complete, this was cooled to room temperature, water was added, and the precipitated crystals were filtered, washed with water and then dried. To a tetrahydrofuran solution (7 mL) of the crystals obtained was added 10% palladium-carbon (100 mg). A hydrogen atmosphere was substituted in the flask, and this was stirred at room temperature for 14 hours. After the reaction was complete, this was filtered through Celite and the filtrate was concentrated. The residue obtained was purified by silica gel column chromatography to yield the title compound (480 mg, 78% yield) as a white solid.

Workup

  1. temperaturethis was heated
  2. temperatureto reflux for 2.5 hours
  3. filtrationthe precipitated crystals were filtered
  4. washwashed with water
  5. customdried
  6. customTo a tetrahydrofuran solution (7 mL) of the crystals obtained
  7. filtrationthis was filtered through Celite
  8. concentrationthe filtrate was concentrated
  9. customThe residue obtained
  10. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-85651393a73141cab71511f81256657d
Source dataset
uspto-grants-2014_09
Patent number
US08829035B2

Reaction notes

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