Butanal → tert-Butyl 8-butyryl-3,4-dihydropyrazino[1,2-a]indole-2(1H)-carboxylate

HRID 1481748노트

반응식

HRID 1481748 반응식
Br[C:2]1[CH:10]=[CH:9][C:8]2[N:7]3[CH2:11][CH2:12][N:13]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:14][C:6]3=[CH:5][C:4]=2[CH:3]=1.CN(C=O)C.N1CCCC1.[CH:32](=[O:36])[CH2:33][CH2:34][CH3:35]>CCOC(C)=O.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1>[C:32]([C:2]1[CH:10]=[CH:9][C:8]2[N:7]3[CH2:11][CH2:12][N:13]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:14][C:6]3=[CH:5][C:4]=2[CH:3]=1)(=[O:36])[CH2:33][CH2:34][CH3:35]

참가 물질

8

반응물 4

HCID 261ButanalHCID 6228DimethylformamideHCID 31268PyrrolidineHCID 712847451,1-Dimethylethyl 8-bromo-3,4-dihydropyrazino[1,2-a]indole-2(1H)-carboxylate

생성물 1

HCID 71284792tert-Butyl 8-butyryl-3,4-dihydropyrazino[1,2-a]indole-2(1H)-carboxylate수율 73%

시약·촉매·용매 3

HCID 634876Binap, (A+-)-촉매HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladium촉매HCID 8857Ethyl Acetate용매

반응 조건

온도
115 °C

실험 절차

To a vial was added tert-butyl 8-bromo-3,4-dihydropyrazino[1,2-a]indole-2(1H)-carboxylate (1.4 g, 4.0 mmol), Pd(dba)2 (75 mg, 2 mol %), BINAP (75 mg, 3 mol %), and crushed 4 Å MS (2.0 g). The vial was evacuated and backfilled under argon. To the vial was then added DMF (15 mL), pyrrolidine (660 μL, 8.0 mmol), and butyraldehyde (1.0 mL, 12 mmol). The vial was then sealed under argon and heated to 115° C. for 6 h. The reaction mixture was then cooled to room temperature, diluted with EtOAc (50 mL), and filtered through celite. The filtrate was washed with H2O (50 mL) and brine (50 mL). The organic layer was dried over Na2SO4, filtered, and concentrated to afford a crude residue that was purified on silica gel (1:1 hexanes/EtOAc) to afford the title compound as a white solid (1.0 g, 73%).

후처리

  1. customcrushed 4 Å MS (2.0 g)
  2. customThe vial was evacuated
  3. customThe vial was then sealed under argon
  4. temperatureThe reaction mixture was then cooled to room temperature
  5. filtrationfiltered through celite
  6. washThe filtrate was washed with H2O (50 mL) and brine (50 mL)
  7. dry with materialThe organic layer was dried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customto afford a crude residue that
  11. customwas purified on silica gel (1:1 hexanes/EtOAc)

출처 및 근거

ORD 기록
ord-fe37c7dc42b44f2c9067944d3ddc7b26
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09409905B2

반응 노트

불러오는 중…