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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
Notes
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Reaction equation

HRID 449954 reaction equation
[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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 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

Product 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

Reagents, catalysts & solvents 4

HCID 24350
Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)
Catalyst
HCID 178418397HCID 178418397, compoundCatalyst
HCID 6228DimethylformamideSolvent
HCID 8857Ethyl AcetateSolvent

Procedure

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]

Workup

  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)

Sources & evidence

ORD record
ord-5ce29cd6aaf84a02854b3cc9dbefa9fb
Source dataset
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08486946B2

Reaction notes

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