Potassium Phosphate, Tribasic → (E)-9-(2-(3,4-difluorophenyl)prop-1-enyl)-1-ethyl-2,6-dimethyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole

HRID 1775986노트

반응식

HRID 1775986 반응식
[CH2:1]([CH:3]1[C:8]2[NH:9][C:10]3[C:15]([C:7]=2[CH2:6][CH2:5][N:4]1[CH3:17])=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=3)[CH3:2].N1CCC[C@H]1C(O)=O.[O-]P([O-])([O-])=O.[K+].[K+].[K+].Br[CH:35]=[C:36]([C:38]1[CH:43]=[CH:42][C:41]([F:44])=[C:40]([F:45])[CH:39]=1)[CH3:37]>CN(C=O)C.[Cu]I>[F:45][C:40]1[CH:39]=[C:38](/[C:36](/[CH3:37])=[CH:35]/[N:9]2[C:10]3[C:15](=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=3)[C:7]3[CH2:6][CH2:5][N:4]([CH3:17])[CH:3]([CH2:1][CH3:2])[C:8]2=3)[CH:43]=[CH:42][C:41]=1[F:44]

참가 물질

7

반응물 4

HCID 62657Potassium Phosphate, TribasicHCID 145742L-ProlineHCID 669117191-ethyl-2,6-dimethyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indoleHCID 866355044-(1-Bromoprop-1-en-2-yl)-1,2-difluorobenzene

생성물 1

HCID 44242798(E)-9-(2-(3,4-difluorophenyl)prop-1-enyl)-1-ethyl-2,6-dimethyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole수율 18.3%

시약·촉매·용매 2

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

실험 절차

1-ethyl-2,6-dimethyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole (82 mg, 0.36 mmol) was dissolved in DMF (6 mL). To this solution was added CuI (8 mg, 0.036 mmol), L-proline (9 mg, 0.086 mmol), K3PO4 (183 mg, 0.86 mmol). The reaction mixture was stirred for 10 min at room temperature followed by addition of 4-(1-bromoprop-1-en-2-yl)-1,2-difluorobenzene (100 mg, 0.43 mmol). The reaction mixture was heated at 80° C. for 18 h. Solvent was evaporated under reduced pressure, the residue was diluted with brine and extracted with ethyl acetate. Organic layer was dried over Na2SO4, and concentrated under reduced pressure. The crude product was purified by silica gel chromatography to obtain 25 mg of (E)-9-(2-(3,4-difluorophenyl)prop-1-enyl)-1-ethyl-2,6-dimethyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole. 1H NMR (DMSO) OXALATE SALT 7.80 (m, 1H), 7.56 (m, 2H), 7.38 (s, 1H), 7.20 (s, 1H), 7.05 (m, 2H), 3.80 (m, 3H), 3.18 (s, 3H), 3.0 (m, 2H), 2.80 (m, 2H), 2.40 (s, 3H), 1.82 (s, 3H), 0.95 (t, 3H).

후처리

  1. temperatureThe reaction mixture was heated at 80° C. for 18 h
  2. customSolvent was evaporated under reduced pressure
  3. additionthe residue was diluted with brine
  4. extractionextracted with ethyl acetate
  5. dry with materialOrganic layer was dried over Na2SO4
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product was purified by silica gel chromatography

출처 및 근거

ORD 기록
ord-86382732ec2e4facb09499e5484f1012
출처 데이터셋
uspto-grants-2016_02
특허 번호
US09260429B2

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