8-Hydroxyquinoline → HCID 66807170, 화합물

HRID 1843995노트

반응식

HRID 1843995 반응식
CC1C=CN=CC=1N1C=CC2NC3C=CC=CC=3C=2C1=O.[C:22]1(=[O:35])[C:34]2[C:33]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[NH:27][C:26]=2[CH:25]=[CH:24][NH:23]1.Br[C:37]1[CH:38]=[N:39][CH:40]=[CH:41][C:42]=1[C:43]([F:46])([F:45])[F:44].OC1C=CC=C2C=1N=CC=C2.C([O-])([O-])=O.[K+].[K+]>[Cu](I)I.CS(C)=O>[F:44][C:43]([F:46])([F:45])[C:42]1[CH:41]=[CH:40][N:39]=[CH:38][C:37]=1[N:23]1[CH:24]=[CH:25][C:26]2[NH:27][C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][C:33]=3[C:34]=2[C:22]1=[O:35]

참가 물질

8

반응물 5

HCID 19238-HydroxyquinolineHCID 11430Potassium CarbonateHCID 121012772,5-dihydro-1H-pyrido[4,3-b]indol-1-oneHCID 199372633-Bromo-4-(trifluoromethyl)pyridineHCID 56941125HCID 56941125, 화합물

생성물 1

HCID 66807170HCID 66807170, 화합물수율 1.5%

시약·촉매·용매 2

HCID 83717Copper iodide촉매HCID 679Dimethyl Sulfoxide용매

실험 절차

Using analogous reaction conditions and work up as described for the preparation of 62A above, 2,5-dihydro-1H-pyrido[4,3-b]indol-1-one (I-62a: 200 mg, 1.08 mmol) was reacted with 3-bromo-4-trifluoromethylpyridine (368.4 mg, 1.63 mmol), 8-hydroxy quinoline (31.3 mg, 0.216 mmol), K2CO3 (223.5 mg, 1.62 mmol), copper iodide (41.14 mg, 0.216 mmol) and DMSO (5 mL) to afford the crude product. Purification by column chromatography on silica gel (2% methanol in DCM), followed by preparative HPLC afforded 5 mg of the product (1.5% yield).

후처리

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

출처 및 근거

ORD 기록
ord-7adf1c703b604a279a221433260b2f0a
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08946260B2

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