Cesium fluoride → HCID 86680300, compound

HRID 2360680Notes

Reaction equation

HRID 2360680 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]([C:16]2[C:17]3[C:25]([CH3:26])=[N:24][N:23]([CH:27]4[CH2:32][CH2:31][CH2:30][CH2:29][O:28]4)[C:18]=3[N:19]=[C:20](Cl)[CH:21]=2)=[O:15])[C:10]([CH3:39])([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[O:40]1[CH2:45][CH2:44][CH2:43][CH2:42][CH:41]1[O:46][C:47]1[CH:52]=[CH:51][C:50](B(O)O)=[CH:49][CH:48]=1.[F-].[Cs+]>CN(C=O)C.C1(C)C=CC=CC=1.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>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]([C:16]2[C:17]3[C:25]([CH3:26])=[N:24][N:23]([CH:27]4[CH2:32][CH2:31][CH2:30][CH2:29][O:28]4)[C:18]=3[N:19]=[C:20]([C:50]3[CH:51]=[CH:52][C:47]([O:46][CH:41]4[CH2:42][CH2:43][CH2:44][CH2:45][O:40]4)=[CH:48][CH:49]=3)[CH:21]=2)=[O:15])[C:10]([CH3:39])([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 25953Cesium fluorideHCID 50176524-(Tetrahydro-2H-pyran-2-yloxy)phenylboronic Acid (contains varying amounts of Anhydride)HCID 86680298HCID 86680298, compound

Product 1

HCID 86680300HCID 86680300, compoundYield 936,785.188%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 21735183Dimethylformamide tolueneSolvent

Conditions

Temperature
100 °C

Procedure

4-[6-Chloro-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine-4-carbonyl]-3-methyl-3-phenyl-piperazine-1-carboxylic acid tert-butyl ester (255 mg) and 4-(tetrahydro-2H-pyran-2-yloxy)phenylboronic acid (153 mg) were dissolved in DMF/toluene (v/v=1/1, 7.5 mL). After inertisation of the mixture with argon; cesium fluoride (140 mg) and tetrakis(triphenylphosphine)palladium(0) (27 mg) were added. The mixture was stirred at 100° C. overnight. The mixture was filtered through a 0.2 μm membrane syringe filter, the filtrate was diluted with ethyl acetate and washed three times with water (15 mL each) and once with brine (10 mL). The organic phase was dried over magnesium sulfate and concentrated. The residue was absorbed on silica and purified by flash chromatography (heptane/ethylacetate v/v=1/1). 3000 g (94%) of the title compound were obtained.

Workup

  1. filtrationThe mixture was filtered through a 0.2 μm membrane syringe
  2. filtrationfilter
  3. additionthe filtrate was diluted with ethyl acetate
  4. washwashed three times with water (15 mL each)
  5. dry with materialThe organic phase was dried over magnesium sulfate
  6. concentrationconcentrated
  7. customThe residue was absorbed on silica
  8. custompurified by flash chromatography (heptane/ethylacetate v/v=1/1)

Sources & evidence

ORD record
ord-fb9db260bfab4d11a2b9d1a93348f17f
Source dataset
uspto-grants-2014_04
Patent number
US08686150B2

Reaction notes

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