Potassium Carbonate → HCID 86630678, compound

HRID 1851203Notes

Reaction equation

HRID 1851203 reaction equation
Br[C:2]1[CH:3]=[N:4][N:5]2[CH:10]=[C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:8]([C:17]3[CH:24]=[CH:23][C:20]([CH:21]=[O:22])=[CH:19][CH:18]=3)=[N:7][C:6]=12.[CH2:25]([Sn](CCCC)(CCCC)C=C)[CH2:26]CC.C([O-])([O-])=O.[K+].[K+]>[Cl-].C([N+](CC)(CC)CC)C.C1COCC1.O.ClCCl.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:11]1([C:9]2[C:8]([C:17]3[CH:24]=[CH:23][C:20]([CH:21]=[O:22])=[CH:19][CH:18]=3)=[N:7][C:6]3[N:5]([N:4]=[CH:3][C:2]=3[CH:25]=[CH2:26])[CH:10]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

9

Reactant 3

HCID 11430Potassium CarbonateHCID 81998TributylvinyltinHCID 86630675HCID 86630675, compound

Product 1

HCID 86630678HCID 86630678, compound

Reagents, catalysts & solvents 5

HCID 5946Tetraethylammonium ChlorideCatalystHCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

400 mg 4-(3-bromo-6-phenylpyrazolo[1,5-a]pyrimidin-5-yl)benzaldehyde (prepared as described above), 504 mg tributyl(vinyl)stannane, 176 mg tetraethylammonium chloride, 147 mg K2CO3 and 19 mg Pd(PPh3)2Cl2 were suspended in 10 mL THF under a nitrogen atmosphere. The mixture was heated (microwave irradiation) to 110° C. for 45 min. This mixture was worked up by diluting with water and extraction with dichloromethane. The combined organic layers were dried over Na2SO4 and concentrated to yield the crude product, which was purified by chromatography on silica gel (ethyl acetate/dichloromethane).

Workup

  1. temperatureThe mixture was heated
  2. custom(microwave irradiation) to 110° C. for 45 min
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-6d59f3ab7bb145178d72fbd44e4f57cc
Source dataset
uspto-grants-2015_02
Patent number
US08957064B2

Reaction notes

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