6-BROMOPYRIDINE-2,3-DIAMINE synthesis
- Product Name:6-BROMOPYRIDINE-2,3-DIAMINE
- CAS Number:129012-04-0
- Molecular formula:C5H6BrN3
- Molecular Weight:188.03
84487-04-7
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129012-04-0
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Yield: 60%
Reaction Conditions:
with acetic acid;zinc in methanol;ethanol at 0 - 20; for 15 h;
Steps:
78.1
Step 1: To a stirred mixture of 6-bromo-3-nitro-2-pyridinamine (2.5 g, 11.47 mmol) in a mixture of glacial HOAc(10 mL), MeOH (10 mL) and EtOH (10 mL) at 0 °C was added portionwise zinc dust (3.73 g, 57.35 mmol). The mixturewas stirred at rt for 15 h. The mixture was filtered through Celite, and the filtrate was concentrated under reducedpressure. The residue was partitioned between saturated aq NaHO3 and EtOAc. The organic layer was separated andthe aqueous layer was extracted with additional EtOAc. The combined organic layers were washed with brine, separatedand dried over MgSO4, filtered, and concentrated under reduced pressure to afford 6-bromopyridine-2,3-diamine (1.30g, 60%) as a solid that did not require further purification. 1H NMR (300 MHz, DMSO-d6) δ 6.61 (d, J = 7.7 Hz, 1H), 6.47(d, J = 7.7 Hz, 1H), 5.82 (s, 2H), 4.79 (s, 2H). LCMS (ESI) m/z 188 and 190 (M+H)+.
References:
Ambit Biosciences Corporation;HADD, Michael J.;HOCKER, Michael D.;HOLLADAY, Mark W.;LIU, Gang;ROWBOTTOM, Martin W.;XU, Shimin EP2766359, 2016, B1 Location in patent:Paragraph 0578
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129012-04-0
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