Cesium fluoride → HCID 86613182, compound

HRID 746807Notes

Reaction equation

HRID 746807 reaction equation
[F-].[Cs+].Br[C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:14]([NH:15][S:16]([CH:19]([CH3:21])[CH3:20])(=[O:18])=[O:17])=[CH:13][CH:12]=[N:11]2)=[CH:6][CH:5]=1.C([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1B(O)O)#N>COCCOC.C1C=CC([PH+]([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.C1C=CC([PH+]([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.C(Cl)Cl.Cl[Pd]Cl.[Fe]>[C:4]1([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:9]=[CH:8][C:7]([N:10]2[C:14]([NH:15][S:16]([CH:19]([CH3:21])[CH3:20])(=[O:18])=[O:17])=[CH:13][CH:12]=[N:11]2)=[CH:6][CH:5]=1

Participants

6

Reactant 3

HCID 25953Cesium fluorideHCID 27346102-Cyanophenylboronic acidHCID 86613171HCID 86613171, compound

Product 1

HCID 86613182HCID 86613182, compoundYield 36.4%

Reagents, catalysts & solvents 2

HCID 53485975CID 53485975CatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
85 °C

Procedure

Add cesium fluoride (0.221 g, 1.45 mmol) and dichloro[1,1′bis(diphenylphosphino)ferrocene]palladium (II) dichloromethane adduct (0.024 g, 0.029 mmol) to a mixture of propane-2-sulfonic acid [2-(4-bromo-phenyl)-2H-pyrazol-3-yl]-amide (0.100 g, 0.290 mmol) and 2-cyanophenylboronic acid (0.043 g, 0.290 mmol) in anhydrous 1,2-dimethoxyethane (5.0 mL). Deoxygenate the mixture three times, immerse into a pre-heated (85° C.) oil bath, and stir for 30 h. Dilute the mixture with water and dichloromethane, filter through Celite®, and wash through with dichloromethane. Concentrate the mixture, re-dissolve in dichloromethane, adsorb onto silica gel, and subject to silica gel flash column chromatography (12 g column, eluting with a gradient of 0-10% methanol/dichloromethane for 40 min., followed by (20% 2.0M NH3 in methanol/dichloromethane) to yield the title product as a light brown solid (0.036 g, 34%): mass spectrum (m/e): 367.0 (M+1), 365.0 (M−1).

Workup

  1. customDeoxygenate the mixture three times
  2. additionDilute the mixture with water and dichloromethane
  3. filtrationfilter through Celite®
  4. washwash through with dichloromethane
  5. concentrationConcentrate the mixture
  6. dissolutionre-dissolve in dichloromethane
  7. washeluting with a gradient of 0-10% methanol/dichloromethane for 40 min.

Sources & evidence

ORD record
ord-b18591a59a704a0998a6dccccd952439
Source dataset
uspto-grants-2008_07
Patent number
US07393868B2

Reaction notes

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