Potassium Phosphate, Tribasic → 8-Fluoro-2-(4-methylpyridine-3-yl) 3,4-dihydro-2H-benzo[4,5]thieno[3,2-c]pyridin-1-one

HRID 1843963

반응식

HRID 1843963 반응식
ClC1C=[C:10]2[C:5]([CH2:6][CH2:7][N:8](C3C=NC=CC=3)[C:9]2=O)=[CH:4]C=1.[F:19][C:20]1[CH:21]=[CH:22][C:23]2[S:31][C:30]3[CH2:29][CH2:28][NH:27][C:26](=[O:32])[C:25]=3[C:24]=2[CH:33]=1.IC1C=NC=CC=1C.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>[Cu](I)I.O1CCOCC1>[F:19][C:20]1[CH:21]=[CH:22][C:23]2[S:31][C:30]3[CH2:29][CH2:28][N:27]([C:6]4[CH:7]=[N:8][CH:9]=[CH:10][C:5]=4[CH3:4])[C:26](=[O:32])[C:25]=3[C:24]=2[CH:33]=1

참가 물질

7

반응물 4

HCID 62657Potassium Phosphate, TribasicHCID 144235133-Iodo-4-methylpyridineHCID 569427267-Chloro-2-pyridin-3-yl-3,4-dihydro-2H-isoquinolin-1-oneHCID 899641758-fluoro-3,4-dihydro-2H-benzo[4,5]thieno[3,2-c]pyridin-1-one

생성물 1

HCID 569409768-Fluoro-2-(4-methylpyridine-3-yl) 3,4-dihydro-2H-benzo[4,5]thieno[3,2-c]pyridin-1-one수율 67.37%

시약·촉매·용매 2

HCID 83717Copper iodide촉매HCID 312751,4-Dioxane용매

실험 절차

Using analogous conditions and workup as described for the preparation of Compound 1A, 8-Fluoro-3,4-dihydro-2H-benzo[4,5]thieno[3,2-c]pyridin-1-one (I-50 g: 100 mg, 0.452 mmol) was reacted with 3-iodo-4-methylpyridine (99.09 mg, 0.452 mmol), 1,4-dioxane (5 mL), copper iodide (8.64 mg, 0.0452 mmol), trans-N,N′-dimethyl-cyclohexyl-1,2-diamine (19.25 mg, 0.1356 mmol) and potassium phosphate (287.44 mg, 1.356 mmol) at 115° C. overnight under nitrogen atmosphere to afford the crude product. Purification by column chromatography on silica gel (1.5% methanol in CHCl3) afforded 95 mg of the product (67.37% yield).

후처리

  1. customto afford the crude product
  2. customPurification by column chromatography on silica gel (1.5% methanol in CHCl3)

출처 및 근거

ORD 기록
ord-c3cb0b60a6b047cfba052866f37376d1
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08946260B2

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