Potassium Phosphate, Tribasic → (E)-3,9-dimethyl-6-(2-(pyridin-3-yl)prop-1-enyl)-1,2,3,4,5,6-hexahydroazepino[4,5-b]indole

HRID 1045605노트

반응식

HRID 1045605 반응식
[CH3:1][N:2]1[CH2:15][CH2:14][C:13]2[C:12]3[CH:11]=[C:10]([CH3:16])[CH:9]=[CH:8][C:7]=3[NH:6][C:5]=2[CH2:4][CH2:3]1.N1CCC[C@H]1C(O)=O.[O-]P([O-])([O-])=O.[K+].[K+].[K+].Br[CH:34]=[C:35]([C:37]1[CH:38]=[N:39][CH:40]=[CH:41][CH:42]=1)[CH3:36]>CN(C=O)C.[Cu]I>[CH3:1][N:2]1[CH2:15][CH2:14][C:13]2[C:12]3[CH:11]=[C:10]([CH3:16])[CH:9]=[CH:8][C:7]=3[N:6](/[CH:34]=[C:35](/[C:37]3[CH:38]=[N:39][CH:40]=[CH:41][CH:42]=3)\[CH3:36])[C:5]=2[CH2:4][CH2:3]1

참가 물질

7

반응물 4

HCID 62657Potassium Phosphate, TribasicHCID 145742L-ProlineHCID 571825283-(1-Bromoprop-1-en-2-yl)pyridineHCID 685600921,2,3,4,5,6-Hexahydro-3,9-dimethylazepino[4,5-b]indole

생성물 1

HCID 59368283(E)-3,9-dimethyl-6-(2-(pyridin-3-yl)prop-1-enyl)-1,2,3,4,5,6-hexahydroazepino[4,5-b]indole

시약·촉매·용매 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 6228Dimethylformamide용매

실험 절차

3,9-Dimethyl-1,2,3,4,5,6-hexahydroazepino[4,5-b]indole (200 mg, 0.934 mmol) was dissolved in DMF (6 mL), CuI (17.7 mg, 0.09 mmol), L-proline (21 mg, 0.18 mmol), K3PO4 (397 mg, 1.86 mmol) was added and stirred for 10 min. at RT. 3-(1-Bromoprop-1-en-2-yl)pyridine (222 mg, 1.12 mmol) was added dropwise and the reaction mixture was heated at 90° C. for 18 h. DMF was evaporated under reduced pressure, 10 mL water was added and the mixture extracted with ethyl acetate. The organic layer was dried over Na2SO4, and concentrated under reduced pressure. The crude compound was purified by column chromatography to 180 mg of the desired compound. 1HNMR (CD3OD, TFA salt) δ (ppm): 9.10 (s, 1H), 8.80 (s, 1H), 8.70 (d, 1H), 8.0 (t, 1H), 7.36 (s, 2H), 7.08 (m, 2H), 3.80 (m, 2H), 3.40 (m, 4H), 3.20 (m, 2H), 3.05 (s, 3H), 2.42 (s, 3H), 1.05 (s, 3H).

후처리

  1. temperaturethe reaction mixture was heated at 90° C. for 18 h
  2. customDMF was evaporated under reduced pressure, 10 mL water
  3. additionwas added
  4. extractionthe mixture extracted with ethyl acetate
  5. dry with materialThe organic layer was dried over Na2SO4
  6. concentrationconcentrated under reduced pressure
  7. customThe crude compound was purified by column chromatography to 180 mg of the desired compound

출처 및 근거

ORD 기록
ord-2acde554a7454f11936d9cb3714f9ae2
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08569287B2

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