Trichloroacetonitrile → Dimethyl-(4-oxazolo[5,4-b]pyridin-2-yl-phenyl)-amine

HRID 40715

Reaction equation

[NH2:1][C:2]1[C:3]([OH:8])=[N:4][CH:5]=[CH:6][CH:7]=1.[CH3:9][N:10]([CH3:20])[C:11]1[CH:19]=[CH:18][C:14]([C:15](O)=O)=[CH:13][CH:12]=1.ClC(Cl)(Cl)C#N>C(#N)C>[CH3:9][N:10]([CH3:20])[C:11]1[CH:19]=[CH:18][C:14]([C:15]2[O:8][C:3]3[C:2]([N:1]=2)=[CH:7][CH:6]=[CH:5][N:4]=3)=[CH:13][CH:12]=1

Participants

Conditions

Temperature: 150 °C

Procedure

3-Amino-pyridin-2-ol (50 mg, 0.45 mmol), 4-dimethylamino-benzoic acid (74 mg, 0.45 mmol), trichloroacetonitrile (91 μL, 0.91 mmol), and polystyrene triphenylphosphine (425 mg, 1.362 mmol) were suspended in acetonitrile (4.5 mL) and heated by microwave to 150° C. for 15 min. The crude reaction mixture was filtered and concentrated affording a residue which was purified by reverse phase chromatography affording dimethyl-(4-oxazolo[5,4-b]pyridin-2-yl-phenyl)-amine (7.1 mg, 0.030 mmol, 6.6% yield). ES MS (M+H+)=240; 1H NMR (300 MHz, CDCl3): δ 8.24 (d, J=5.1 Hz, 1H); 8.14 (d, J=8.6 Hz, 2H); 7.95 (d, J=7.8 Hz, 1H); 7.28 (dd, J=7.7, 4.9 Hz, 2H); 6.78 (d, J=8.6 Hz, 1H); 3.09 (s, 6H); HRMS m/z 240.1122 (C14H13N3O1+H+ requires 240.1132).

Workup

customThe crude reaction mixture
filtrationwas filtered
concentrationconcentrated
customaffording a residue which
customwas purified by reverse phase chromatography

Sources & evidence

ORD record: ord-3daf2858d8c249759d5a0b398ac9e5f0
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08530483B2

Linked notes

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