HCID 86667167、化合物 → HCID 67980763、化合物

HRID 1260160ノート

反応式

HRID 1260160 の反応式
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]

参加物

4

反応物 1

HCID 86667167HCID 86667167、化合物

生成物 1

HCID 67980763HCID 67980763、化合物

試薬・触媒・溶媒 2

HCID 11246Silver acetate触媒HCID 12669390N,N-Dimethylmethanimidamide溶媒

実験手順

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.

後処理

  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%)

出典と根拠

ORDレコード
ord-8acc851f46b3449c8d5e02ad50cd8df3
出典データセット
uspto-grants-2013_06
特許番号
US08470786B2

反応ノート

読み込み中…