Dimethylformamide → HCID 71253450, 화합물

HRID 1775088노트

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HRID 1775088 반응식
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[CH:8]=[C:9]3[C:15]([Sn](C)(C)C)=[N:14][N:13]([CH2:20][O:21][CH2:22][CH2:23][Si:24]([CH3:27])([CH3:26])[CH3:25])[C:10]3=[CH:11][N:12]=2)[CH:2]=1.[Br:28][C:29]1[C:30]([F:36])=[N:31][C:32](I)=[CH:33][CH:34]=1.CN(C)C=O.[F-].[Cs+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cu]I>[Br:28][C:29]1[CH:34]=[CH:33][C:32]([C:15]2[C:9]3[C:10](=[CH:11][N:12]=[C:7]([C:3]4[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=4)[CH:8]=3)[N:13]([CH2:20][O:21][CH2:22][CH2:23][Si:24]([CH3:27])([CH3:26])[CH3:25])[N:14]=2)=[N:31][C:30]=1[F:36]

참가 물질

7

반응물 4

HCID 6228DimethylformamideHCID 25953Cesium fluorideHCID 71253848HCID 71253848, 화합물HCID 717430873-Bromo-2-fluoro-6-iodopyridine

생성물 1

HCID 71253450HCID 71253450, 화합물

시약·촉매·용매 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178418397HCID 178418397, 화합물촉매

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온도
40 °C

실험 절차

To an argon protected mixture of 5-(pyridin-3-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-3-(trimethylstannyl)-1H-pyrazolo[3,4-c]pyridine (239 mg, 0.489 mmol) and 3-bromo-2-fluoro-6-iodopyridine (162.3 mg, 0.538 mmol) in N,N-Dimethylformamide (5 mL, 60 mmol) was added Cesium fluoride (148 mg, 0.98 mmol). Tetrakis(triphenylphosphine)palladium(0) (56.482 mg, 0.048878 mmol) and Copper(I) iodide (18.618 mg, 0.097757 mmol) were then added and the resulting mixture was stirred at 40° C. for 2 hours. The mixture was cooled to room temperature, filtered through Celite®. The filter cake was washed with EtOAc. The organic layer was washed with brine, dried with MgSO4, and then concentrated. The residue was purified on silica eluted with 0 to 100% EtOAc in Heptane to afford 3-(5-bromo-6-fluoropyridin-2-yl)-5-(pyridin-3-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazolo[3,4-c]pyridine as a light yellow oil, which solidified upon standing (208.1 mg, 85%).

후처리

  1. temperatureThe mixture was cooled to room temperature
  2. filtrationfiltered through Celite®
  3. washThe filter cake was washed with EtOAc
  4. washThe organic layer was washed with brine
  5. dry with materialdried with MgSO4
  6. concentrationconcentrated
  7. customThe residue was purified on silica
  8. washeluted with 0 to 100% EtOAc in Heptane

출처 및 근거

ORD 기록
ord-ddf5a3ecb412466a84c8d76e83ff0d27
출처 데이터셋
uspto-grants-2016_02
특허 번호
US09260425B2

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