Benzyl Bromide → methyl 1-benzyl-2-oxo-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazine-7-carboxylate

HRID 2421884노트

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HRID 2421884 반응식
[O:1]=[C:2]1[CH2:7][O:6][C:5]2[N:8]=[CH:9][C:10]([C:12]([O:14][CH3:15])=[O:13])=[CH:11][C:4]=2[NH:3]1.C(=O)([O-])[O-].[K+].[K+].[CH2:22](Br)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>CN(C=O)C.[I-].C([N+](CCCC)(CCCC)CCCC)CCC.CCOC(C)=O.C(=O)(O)[O-].[Na+]>[CH2:22]([N:3]1[C:2](=[O:1])[CH2:7][O:6][C:5]2[N:8]=[CH:9][C:10]([C:12]([O:14][CH3:15])=[O:13])=[CH:11][C:4]1=2)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

참가 물질

8

반응물 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 57896640Methyl 2-oxo-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazine-7-carboxylate

생성물 1

HCID 57896764methyl 1-benzyl-2-oxo-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazine-7-carboxylate

시약·촉매·용매 4

HCID 67553Tetrabutylammonium Iodide촉매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매HCID 516892Sodium Bicarbonate용매

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온도
100 °C

실험 절차

Methyl 2 oxo-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazine-7-carboxylate (50 mg, 240 μmol) was dissolved in DMF (0.5 mL) in a 2 mL microwave vial containing a magnetic stirrer bar. Potassium carbonate (100 mg, 720 μmol) was added to the vial followed by benzyl bromide (62 mg, 360 μmol) and tetrabutylammonium iodide (10 mg, 27 μmol). The vial was capped and was heated to 100° C. by microwave irradiation for 5 minutes. The reaction mixture was diluted with EtOAc (3 mL) and of saturated aqueous sodium bicarbonate (3 mL). The organic layer was removed and the aqueous layer was extracted with 2 mL of EtOAc. The organic layers were combined, dried over anhydrous Na2SO4 filtered and evaporated. This yielded 70 mg of a yellow oil which was used without further purification. LCMS (+ESI) m/z=299.1 [M+H]+.

후처리

  1. additioncontaining a magnetic stirrer bar
  2. customThe vial was capped
  3. customThe organic layer was removed
  4. extractionthe aqueous layer was extracted with 2 mL of EtOAc
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. customevaporated
  8. customThis yielded 70 mg of a yellow oil which was used without further purification

출처 및 근거

ORD 기록
ord-9277d09840f94170be7ed558d64870a1
출처 데이터셋
uspto-grants-2011_06
특허 번호
US07960377B2

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