4-OXAZOLO[4,5-B]PYRIDIN-2-YL-PHENYLAMINE synthesis
- Product Name:4-OXAZOLO[4,5-B]PYRIDIN-2-YL-PHENYLAMINE
- CAS Number:95331-56-9
- Molecular formula:C12H9N3O
- Molecular Weight:211.22
16867-03-1
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150-13-0
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95331-56-9
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Yield:95331-56-9 78%
Reaction Conditions:
with Eaton′s reagent at 180; for 4 h;
Steps:
4.15.1. General procedures for preparation of A22-TM1
A solution of 2-aminopyridin-3-ol (8.0 mmol, 0.88 g), 4-aminobenzoic acid (8.0 mmol, 1.10 g), and Eaton's reagent (10.0 g)were stirred under 180 C for 4 h. Then, the mixture was cooled toroom temperature and poured into ice water (100.0 mL), and thepH value was adjusted to 8.0 with sodium bicarbonate. The organiclayer was extracted with ethyl acetate, washed with brine, driedover Na2SO4, and concentrated in vacuo. The obtained yellow solid was recrystallized from ethyl acetate to give A22-TM1 (1.3 g, 78%)as a yellow solid. 4-(oxazolo[4,5-b]pyridin-2-yl)aniline (A22-TM1) yellow solid.Yield: 78%. 1H NMR (400 MHz, DMSO-d6) d 8.41 (dd, J 5.0, 1.4 Hz,1H), 8.07 (dd, J 8.1, 1.4 Hz, 1H), 7.95e7.87 (m, 2H), 7.31 (dd, J 8.0,5.0 Hz, 1H), 6.75e6.68 (m, 2H), 6.15 (s, 2H). 13C NMR (101 MHz,DMSO-d6) d 166.2,156.4,153.3,145.6,142.3,129.5,119.2,117.8,113.5,111.8, 40.1, 39.9, 39.7, 39.3, 39.1, 38.9. HRMS (ESI) [M H] calcdfor C12H10N3O: 212.0824; found: 212.0827.
References:
Dou, Xiaodong;Sun, Xiaojiao;Huang, Huixia;Jiang, Lan;Jin, Zefang;Liu, Yameng;Zou, Yang;Li, Zhongtang;Zhu, Guiwang;Jin, Hongwei;Jiao, Ning;Zhang, Liangren;Liu, Zhenming;Zhang, Lihe [European Journal of Medicinal Chemistry,2022,vol. 233,art. no. 114196]
![Oxazolo[4,5-b]pyridine](/CAS/GIF/273-97-2.gif)
273-97-2
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540-37-4
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$6.00/5g
95331-56-9
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$45.00/10mg