8-Hydroxyquinoline → HCID 66807170、化合物

HRID 1843995ノート

反応式

HRID 1843995 の反応式
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]

参加物

8

反応物 5

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

生成物 1

HCID 66807170HCID 66807170、化合物収率 1.5%

試薬・触媒・溶媒 2

HCID 83717Copper iodide触媒HCID 679Dimethyl Sulfoxide溶媒

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-7adf1c703b604a279a221433260b2f0a
出典データセット
uspto-grants-2015_02
特許番号
US08946260B2

反応ノート

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