ChemicalBook CAS DataBase List 6-BROMOPYRIDINE-2,3-DIAMINE

6-BROMOPYRIDINE-2,3-DIAMINE synthesis

6synthesis methods

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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$31.00/200 μmol

129012-04-0
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$33.00/100mg

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