Methylamine tetrahydrofuran → 4-(4-bromo-3,5-dimethoxyphenyl)-1-methyl-1H-imidazole

HRID 56501

반응식

HRID 56501 반응식
[Br:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]([CH:10]2O[CH:13]=[N:12][CH:11]2S(C2C=CC(C)=CC=2)(=O)=O)=[CH:4][C:3]=1[O:25][CH3:26].[CH3:27][NH2:28].C1COCC1>CO.CCOC(C)=O>[Br:1][C:2]1[C:3]([O:25][CH3:26])=[CH:4][C:5]([C:10]2[N:28]=[CH:27][N:12]([CH3:13])[CH:11]=2)=[CH:6][C:7]=1[O:8][CH3:9]

참가 물질

4

반응물 2

HCID 66615946Methylamine tetrahydrofuranHCID 673894555-(4-Bromo-3,5-dimethoxyphenyl)-4-tosyl-4,5-dihydrooxazole

생성물 1

HCID 584319944-(4-bromo-3,5-dimethoxyphenyl)-1-methyl-1H-imidazole수율 21%

시약·촉매·용매 1

HCID 21584119Ethylacetate methanol용매

반응 조건

온도
135 °C

실험 절차

To an oven-dried pressure tube was added 5-(4-bromo-3,5-dimethoxyphenyl)-4-tosyl-4,5-dihydrooxazole (0.4 g, 0.91 mmol), methylamine-THF solution (1.8 mL of a 2.0 M solution, 3.6 mmol), and xylenes (5 mL). The tube was sealed under argon then heated at 135° C. for 15 hours. After cooling to room temperature, the reaction mixture was transferred and concentrated in vacuo then partitioned between EtOAc and H2O. The layers were separated and the aqueous layer was extracted with EtOAc. The combined organics were washed with brine twice, dried over Na2SO4 and concentrated. Purification by chromatography (50-100% EtOAc-hexanes then 2-5% MeOH-EtOAc) provided 4-(4-bromo-3,5-dimethoxyphenyl)-1-methyl-1H-imidazole as a light yellow solid (0.056 g, 21% yield).

후처리

  1. customThe tube was sealed under argon
  2. temperatureAfter cooling to room temperature
  3. concentrationconcentrated in vacuo
  4. customthen partitioned between EtOAc and H2O
  5. customThe layers were separated
  6. extractionthe aqueous layer was extracted with EtOAc
  7. washThe combined organics were washed with brine twice
  8. dry with materialdried over Na2SO4
  9. concentrationconcentrated
  10. customPurification by chromatography (50-100% EtOAc-hexanes

출처 및 근거

ORD 기록
ord-fccd77aced164354bdf2c464291341cf
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09434707B2

연결된 노트

불러오는 중…