HCID 86667167, 화합물 → HCID 67980763, 화합물

HRID 1260160노트

반응식

HRID 1260160 반응식
Br[CH:2]1[C:11]2[C:6]3=[C:7]([C:12]([C:14](=[O:20])[C:15]([O:17][CH2:18]C)=[O:16])=[CH:13][N:5]3[CH2:4][CH2:3]1)[CH:8]=[CH:9][CH:10]=2>CN(C)C=N.C([O-])(=O)C.[Ag+]>[CH3:18][O:17][C:15](=[O:16])[C:14]([C:12]1[C:7]2=[C:6]3[C:11](=[CH:10][CH:9]=[CH:8]2)[CH:2]([O:17][C:15](=[O:16])[CH3:14])[CH2:3][CH2:4][N:5]3[CH:13]=1)=[O:20]

참가 물질

4

반응물 1

HCID 86667167HCID 86667167, 화합물

생성물 1

HCID 67980763HCID 67980763, 화합물

시약·촉매·용매 2

HCID 11246Silver acetate촉매HCID 12669390N,N-Dimethylmethanimidamide용매

실험 절차

To a solution of ethyl (6-bromo-5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)(oxo)acetate (890 mg, 2.76 mmol) in dimethylformamidine (20 mL) at 0° C. was added silver acetate (458 mg, 2.76 mmol). The reaction mixture was allowed to warm to room temperature and stirred for 2 hr. The mixture was filtered through Celite and rinsed with ethyl acetate (100 mL). The filtrated was diluted with water (100 mL) and extracted with ethyl acetate (3×100 mL). The combined organic layers were washed saturated aqueous sodium chloride solution (50 mL) dried over anhydrous sodium sulfate, and evaporated to dryness. The residue was purified by silica gel chromatography, eluting with a ethyl acetate/hexanes (10-60%) to methyl[6-(acetyloxy)-5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl](oxo)acetate as a yellow solid (326 mg, 39%). Mp: 165-168° C.; 1H NMR (CDCl3) 400 MHz δ: 8.39 (s, 1H), 8.29 (d, J=7.4 Hz, 1H), 7.31-7.36 (m, 2H), 6.22 (t, J=3.5 Hz, 1H), 4.33-4.36 (m, 2H), 4.41-4.43 (m, 1H), 3.95 (s, 3H), 2.44-2.47 (m, 1H), 2.36-2.39 (m, 1H); LCMS [M+H]: 302.

후처리

  1. filtrationThe mixture was filtered through Celite
  2. washrinsed with ethyl acetate (100 mL)
  3. additionThe filtrated was diluted with water (100 mL)
  4. extractionextracted with ethyl acetate (3×100 mL)
  5. washThe combined organic layers were washed saturated aqueous sodium chloride solution (50 mL)
  6. dry with materialdried over anhydrous sodium sulfate
  7. customevaporated to dryness
  8. customThe residue was purified by silica gel chromatography
  9. washeluting with a ethyl acetate/hexanes (10-60%) to methyl[6-(acetyloxy)-5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl](oxo)acetate as a yellow solid (326 mg, 39%)

출처 및 근거

ORD 기록
ord-8acc851f46b3449c8d5e02ad50cd8df3
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08470786B2

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