ChemicalBook CAS DataBase List CHEMBRDG-BB 9038439

CHEMBRDG-BB 9038439 synthesis

5synthesis methods

Product Name:CHEMBRDG-BB 9038439
CAS Number:33922-96-2
Molecular formula:C9H10BrNO2
Molecular Weight:244.09

67-56-1 Synthesis

67-56-1
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6-BROMO-1-METHYL-1H-BENZO[D][1,3]OXAZINE-2,4-DIONE

22721-17-1
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33922-96-2
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Yield:33922-96-2 7.41 g

Reaction Conditions:

with dmap in N,N-dimethyl-formamide at 50; for 4 h;Inert atmosphere;

Steps:

4.2.17 Gram-scale synthesis of compound 16

Crude 6-bromo-1-methyl-1H-benzo[d][1,3]oxazine-2,4-dione was dissolved in DMF (41 mL) and MeOH (12 mL) before DMAP (994.5 mg, 8.14 mmol) was added. The mixture was heated for 4 h at 50 °C. Upon cooling, water and EtOAc were added, and the organic layer was separated. The aqueous layer was extracted with EtOAc (60 mL x 3). The combined organic layers were washed with brine and dried over Na₂SO₄, filtered and concentrated under reduced pressure afforded the crude product, which was further purified by flash chromatography (50/1 PE/EtOAc) afforded compound 16 (7.41 g, 75%, 3 steps) as a pale yellow solid. m.p. 67.8-68.8 °C. ¹H NMR (400 MHz, CDCl₃) δ 7.98 (d, J=2.4 Hz, 1H), 7.61 (brs, 1H), 7.24 (dd, J=8.8 Hz, 2.4 Hz, 1H), 6.55 (d, J=8.8 Hz, 1H), 3.85 (s, 3H), 2.88 (s, 3H).

References:

Xu, Yuan-Ze;Wen, Qi-Ling;Sha, Feng;Li, Qiong;Wu, Xin-Yan [Tetrahedron,2021,vol. 92]

5794-88-7 Synthesis