Dimethyl Sulfoxide → ethyl 2-methyl-1H-indole-3-carboxylate

HRID 1526949

반응식

HRID 1526949 반응식
CS(C)=O.I[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[NH2:12].O=[C:14]([CH3:21])[CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17].C(=O)([O-])[O-].[Cs+].[Cs+]>[Cu-]=O.O>[CH3:21][C:14]1[NH:12][C:7]2[C:6]([C:15]=1[C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:11][CH:10]=[CH:9][CH:8]=2

참가 물질

7

반응물 4

HCID 679Dimethyl SulfoxideHCID 8868Ethyl AcetoacetateHCID 10796Cesium carbonateHCID 119952-Iodoaniline

생성물 1

HCID 4072358ethyl 2-methyl-1H-indole-3-carboxylate수율 15.1%

시약·촉매·용매 2

HCID 178419072HCID 178419072, 화합물촉매HCID 962Water용매

반응 조건

온도
100 °C

실험 절차

To a mixed solution of dimethyl sulfoxide and water (20 mL), 2-iodobenzenamine (3.0 g, 13.7 mmol), ethyl 3-oxobutanoate (2.0 g, 15.1 mmol), copper(I) oxide (0.2 g, 1.4 mmol) and cesium carbonate (4.5 g, 13.7 mmol) was added. The mixture was stirred at 100° C. for 9 hours under nitrogen gas atmosphere. The reaction mixture was filtered through a pad of celite. The filtrate was diluted with water and extracted with ethyl acetate. The organic phase was concentrated in vacuo, and then the residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate=5:1) to give ethyl 2-methyl-1H-indole-3-carboxylate as a light yellow solid (0.42 g, 15%). 1H NMR (300 MHz, CDCl3): δ 8.12-8.09 (m, 1H), 7.31-7.16 (m, 3H), 4.40 (q, J=6.9 Hz, 2H), 2.77 (s, 3H), 1.45 (t, J=6.9 Hz, 3H).

후처리

  1. filtrationThe reaction mixture was filtered through a pad of celite
  2. additionThe filtrate was diluted with water
  3. extractionextracted with ethyl acetate
  4. concentrationThe organic phase was concentrated in vacuo
  5. customthe residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate=5:1)

출처 및 근거

ORD 기록
ord-bb1e46f6229547b2979abf4b7300b792
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09085583B2

연결된 노트

불러오는 중…