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Cesium fluoride → 2-(2-Fluorophenyl)-5-{[4-(1,3-thiazol-4-yl)phenyl]methyl}-2,5-dihydro-3H-pyrazolo[4,3-c]cinnolin-3-one

HRID 449954
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HRID 449954 반응식
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:28](=[O:29])[C:11]2=[N:12][N:13]([CH2:20][C:21]3[CH:26]=[CH:25][C:24](I)=[CH:23][CH:22]=3)[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:19]=3[C:10]2=[N:9]1.C([Sn](CCCC)(CCCC)[C:35]1[N:36]=[CH:37][S:38][CH:39]=1)CCC.[F-].[Cs+]>CN(C)C=O.C(OCC)(=O)C.[Cu]I.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>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:28](=[O:29])[C:11]2=[N:12][N:13]([CH2:20][C:21]3[CH:26]=[CH:25][C:24]([C:35]4[N:36]=[CH:37][S:38][CH:39]=4)=[CH:23][CH:22]=3)[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:19]=3[C:10]2=[N:9]1
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참가 물질

8

반응물 3

HCID 25953Cesium fluorideHCID 27632584-(Tri-n-butylstannyl)thiazoleHCID 468965122-(2-fluorophenyl)-5-[(4-iodophenyl)methyl]-2,5-dihydro-3H-pyrazolo[4,3-c]cinnolin-3-one

생성물 1

HCID 468965132-(2-Fluorophenyl)-5-{[4-(1,3-thiazol-4-yl)phenyl]methyl}-2,5-dihydro-3H-pyrazolo[4,3-c]cinnolin-3-one

시약·촉매·용매 4

HCID 24350
Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)
촉매
HCID 178418397HCID 178418397, 화합물촉매
HCID 6228Dimethylformamide용매
HCID 8857Ethyl Acetate용매

실험 절차

2-(2-Fluorophenyl)-5-[(4-iodophenyl)methyl]-2,5-dihydro-3H-pyrazolo[4,3-c]cinnolin-3-one [(Example 19) 25 mg, 0.050 mmol] and 4-(tributylstannyl)thiazole (28 mg, 0.076 mmole, 1.5 equiv) were dissolved in degassed N,N-dimethylformamide (1 mL) and treated with cesium fluoride (15 mg, 0.101 mmol, 2 equiv), copper(I)iodide (4 mg, 0.020 mmol, 0.4 equiv), and tetrakis(triphenylphosphine)palladium(0) (12 mg, 0.010 mmol, 0.2 equiv). The mixture was stirred at ambient temperature for one hour, diluted with ethyl acetate (15 mL) and filtered. The solids were discarded, the filtrate was concentrated in vacuo and the residue was purified by preparative reverse phase HPLC (20:80 to 80:20; acetonitrile containing 0.1% trifluoroacetic acid:water containing 0.1% trifluoroacetic acid), providing the titled compound: 1H-NMR (400 MHz, CDCl3) δ 8.99 (1H, s), 8.34 (1H, d, J=8.3 Hz), 7.89 (2H, d, J=8.2 Hz), 7.69-7.55 (6H, m), 7.41 (2H, d, J=8.2 Hz), 7.32-7.24 (2H, m), 5.90 (2H, s) ppm; low resolution mass spectrometry (ES+) m/z 453.9 [(M+H)+; calculated for C25H16FN5OS: 453.4]

후처리

  1. filtrationfiltered
  2. concentrationthe filtrate was concentrated in vacuo
  3. customthe residue was purified by preparative reverse phase HPLC (20:80 to 80:20; acetonitrile containing 0.1% trifluoroacetic acid:water containing 0.1% trifluoroacetic acid)

출처 및 근거

ORD 기록
ord-5ce29cd6aaf84a02854b3cc9dbefa9fb
출처 데이터셋
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08486946B2

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