6-bromo-5-methyl-3,4-dihydro-2H-benzo[b][1,4]oxazine synthesis

4synthesis methods

Product Name:6-bromo-5-methyl-3,4-dihydro-2H-benzo[b][1,4]oxazine
CAS Number:1154740-48-3
Molecular formula:C9H10BrNO
Molecular Weight:228.09

6-bromo-5-methyl-2H-benzo[b][1,4]oxazin-3(4H)-one

1154740-47-2
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6-bromo-5-methyl-3,4-dihydro-2H-benzo[b][1,4]oxazine

1154740-48-3
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Yield:1154740-48-3 86%

Reaction Conditions:

with borane-THF in tetrahydrofuran at 0 - 20; for 42 h;Inert atmosphere;

Steps:

W.a a) 6-Bromo-5-methyl-3,4-dihydro-2H-benzo[1,4]oxazine

a)
6-Bromo-5-methyl-3,4-dihydro-2H-benzo[1,4]oxazine
A solution of 6-bromo-5-methyl-4H-benzo[1,4]oxazin-3-one (CAS registry 1154740-47-2) (425 mg, 1.56 mmol) in THF (9 ml) was treated under argon at 0° C. with BH₃*THF (1M in THF, 4.7 ml, 4.69 mmol) and stirred for 18 h at rt. BH₃.THF 1M (2 ml) was added and stirring was continued for another 24 h.
The reaction mixture was concentrated and purified by flash chromatography on silica gel (cyclohexane/EtOAc 100:0 to 80:20) to afford the title compound as an orange solid (324 mg, 86% yield)
HPLC Rt_M1=1.04 min; ESIMS: 228, 230 [(M+H)⁺].
¹H NMR (400 MHz, DMSO-d₆): δ 6.68 (d, 1H), 6.48 (d, 1H), 5.54 (br s, 1H), 4.04 (t, 2H), 3.36-3.26 (m, 2H), 2.11 (s, 3H).

References:

US2013/165436,2013,A1 Location in patent:Paragraph 0664; 0665; 0666

4920-77-8
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1154740-48-3
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References

85598-12-5
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$21.00/100mg

1154740-48-3
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1154740-46-1 Synthesis

1154740-46-1
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1154740-48-3
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References