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Structure of 1154740-47-2

Chemical Structure| 1154740-47-2

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Product Details of [ 1154740-47-2 ]

CAS No. :1154740-47-2
Formula : C9H8BrNO2
M.W : 242.07
SMILES Code : O=C1NC2=C(C)C(Br)=CC=C2OC1
MDL No. :MFCD20527815

Safety of [ 1154740-47-2 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319
Precautionary Statements:P261-P302+P352-P305+P351+P338

Application In Synthesis of [ 1154740-47-2 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 1154740-47-2 ]

[ 1154740-47-2 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 1154740-47-2 ]
  • [ 1154740-48-3 ]
YieldReaction ConditionsOperation in experiment
86% With borane-THF; In tetrahydrofuran; at 0 - 20℃; for 42h;Inert atmosphere; 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 RtM1=1.04 min; ESIMS: 228, 230 [(M+H)+]. 1H NMR (400 MHz, DMSO-d6): delta 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).
81% Step 4:To an ice cold THF (6 mL) solution of the cyclic amide 5d (280 mg, 1.16 mmol) under nitrogen, a borane-THF solution (1M in THF, 1.74 mL, 1.74 mmol) is added slowly. The reaction mixture is slowly allowed to warm to RT, then is stirred at RT for approximately 1.5 h and then gently heated to reflux for 1 h to complete the conversion. The mixture is cooled in an ice bath and is carefully quenched with aqueous 1 M NaOH (4 mL) over 10 min. The reaction mixture is partitioned between EtOAc (150 mL) and water (25 mL). The organic layer is washed with aqueous 1 N <n="57"/>NaOH (20 ml_), saturated aqueous NaCI, and finally dried over anhydrous MgSO4, filtered and concentrated to give the crude 5e as an amber oil (212 mg, 81% yield). This product is used as such for next transformation.
81% To an ice cold THF (6 mL) solution of the cyclic amide 5d (280 mg, 1.16 mmol) under nitrogen, a borane-THF solution (1M in THF, 1.74 mL, 1.74 mmol, 1 ,5 eq) is added slowly. The reaction mixture is slowly allowed to warm to RT, then is stirred at RT for approximately 1.5 h and then gently heated to reflux for about 1 h to complete the conversion. The mixture is cooled in an ice bath and is carefully quenched with aqueous 1 M NaOH (4 mL) over about 10 min. The reaction mixture is partitioned between EtOAc (150 mL) and water (25 mL). The organic layer is washed with aqueous 1 N NaOH (20 mL), saturated aqueous NaCI, and finally dried over anhydrous MgSO4, filtered and concentrated to give the crude 5e as an amber oil (212 mg, 81% yield). This product is used as such for next transformation.
81% With borane-THF; In tetrahydrofuran; at 0 - 25℃; for 2.5h;Heating / reflux; To an ice cold THF (6 mL) solution of the cyclic amide 5d (280 mg, 1 16 mmol) under nitrogen, a borane-THF solution (1 M in THF, 1 74 mL, 1 74 mmol) is added slowly The reaction mixture is slowly allowed to warm to RT, then is stirred at RT for approximately 1 5 h and then gently heated to reflux for 1 h to complete the conversion The mixture is cooled in an ice bath and is carefully quenched with aqueous 1 M NaOH (4 mL) over 10 mm The reaction mixture is partitioned between EtOAc (150 mL) and water (25 mL) The organic layer is washed with aqueous 1 N NaOH (20 mL) and brine, dried over anhydrous MgSO4, filtered and concentrated to give the crude 5e as an amber oil (212 mg, 81 % yield) This product is used as such for next transformation
81% With borane-THF; In tetrahydrofuran; at 0 - 20℃; for 2.5h;Heating / reflux; To an ice cold THF (6 mL) solution of the cyclic amide 5d (280 mg, 1.16 mmol) under nitrogen, a borane-THF solution (1 M in THF, 1.74 mL, 1.74 mmol) is added slowly. The reaction mixture is slowly allowed to warm to RT, then is stirred at RT for 1.5 h and then gently heated to reflux for 1 h to complete the conversion. The mixture is cooled in an ice bath and is carefully quenched with aqueous 1 M NaOH (4 mL) over 10 min. The reaction mixture is partitioned between EtOAc (150 mL) and water (25 mL). The organic layer is washed with aqueous 1 N NaOH (20 mL), saturated aqueous NaCI, and finally dried over anhydrous MgSO4, filtered and concentrated to give the crude 5e as an amber oil (212 mg, 81% yield). This product is used as such for next transformation.
With borane-THF; In tetrahydrofuran; at 20℃; under 760.051 Torr; for 2.5h;Cooling with ice; An ice cold mixture of 6-bromo-5-methyl-2H-1 ,4-benzoxazin-3(4H)-one (3.05 g, 12.59 mmol) in tetrahydrofuran (THF) (40 mL) was treated with borane tetrahydrofuran complex (1 .0 M solution in tetrahydrofuran (18.88 mL, 18.88 mmol) and the mixture was stirred at ambient temperature for 150 minutes. The mixture was cooled to 0 C and then quenched slowly with 1 N NaOH (30 mL). The mixture was extracted with ethyl acetate, then washed with 1 N NaOH, dried over sodium sulfate, filtered and then concentrated to a thick dark brown oil. The material was purified on silica gel (95:4:1 dichloromethane/methanol/ammonium hydroxide, gradient) to afford an off-white solid: 1H NMR (400MHz, CHLOROFORM-d) delta ppm 6.87 (d, J = 8.6 Hz, 1 H), 6.57 (d, J = 8.8 Hz, 1 H), 4.31 - 4.15 (m, 2 H), 3.56 - 3.38 (m, 2 H), 2.22 (s, 3 H); LC/MS (m/z) ES+ = 228 (M+1 ).

 

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[ 1154740-47-2 ]

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