3-Bromopyridine → 2-Pyridin-3-yl-7-trifluoromethyl-3,4-dihydro-2H-isoquinolin-1-one

HRID 1843865

반응식

HRID 1843865 반응식
[F:1][C:2]([F:15])([F:14])[C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][NH:9][C:10]2=[O:13])=[CH:5][CH:4]=1.Br[C:17]1[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>[Cu](I)I.O1CCOCC1>[N:19]1[CH:20]=[CH:21][CH:22]=[C:17]([N:9]2[CH2:8][CH2:7][C:6]3[C:11](=[CH:12][C:3]([C:2]([F:1])([F:14])[F:15])=[CH:4][CH:5]=3)[C:10]2=[O:13])[CH:18]=1

참가 물질

6

반응물 3

HCID 122863-BromopyridineHCID 62657Potassium Phosphate, TribasicHCID 668015937-(Trifluoromethyl)-3,4-dihydroisoquinolin-1(2H)-one

생성물 1

HCID 569427312-Pyridin-3-yl-7-trifluoromethyl-3,4-dihydro-2H-isoquinolin-1-one수율 22.1%

시약·촉매·용매 2

HCID 83717Copper iodide촉매HCID 312751,4-Dioxane용매

실험 절차

Using analogous reaction conditions as described in Example 1, 7-trifluoromethyl-3,4-dihydro-2H-isoquinolin-1-one (I-16c: 150 mg, 0.698 mmol) was reacted with 3-bromo-pyridine (220 mg, 1.395 mmol), 1,4-dioxane (10 mL), copper iodide (13.29 mg, 0.0698 mmol), trans-N,N′-dimethyl-cyclohexyl-1,2-diamine (29.33 mg, 0.209 mmol) and potassium phosphate (369.9 mg, 1.745 mmol) to afford the crude product. Purification by column chromatography on silica gel (1.5% methanol in DCM) afforded 45 mg of the product (22.05% yield).

후처리

  1. customreaction conditions
  2. customto afford the crude product
  3. customPurification by column chromatography on silica gel (1.5% methanol in DCM)

출처 및 근거

ORD 기록
ord-8f90849e00324bf8939ff1b8d4dd3eea
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08946260B2

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