Tetrahydrofuran → HCID 86630678, compound

HRID 1915570Notes

Reaction equation

HRID 1915570 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.C([O-])([O-])=O.[K+].[K+].[CH2:31]1COC[CH2:32]1>[Cl-].C([N+](CC)(CC)CC)C.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:31]=[CH2:32])[CH:10]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

8

Reactant 3

HCID 8028TetrahydrofuranHCID 11430Potassium CarbonateHCID 86630675HCID 86630675, compound

Product 1

HCID 86630678HCID 86630678, compound

Reagents, catalysts & solvents 4

HCID 5946Tetraethylammonium ChlorideCatalystHCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

400 mg 4-(3-bromo-6-phenylpyrazolo[1,5-a]pyrimidin-5-yl)benzaldehyde (prepared as described under example 31), 504 mg tributyl(vinyl)stanane, 176 mg tetraethylammonium chloride, 147 mg K2CO3 and 19 mg Pd(PPh3)2Cl2 are suspended in 10 ml THF under a nitrogen atmosphere. The mixture is heated (microwave irradiation) to 110° C. for 45 min. This mixture is worked up by diluting with water and extraction with dichloromethane. The combined organic layers are dried over Na2SO4 and concentrated to yield the crude product, which is purified by chromatography on silica gel (ethyl acetate/dichloromethane).

Workup

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

Sources & evidence

ORD record
ord-9fa5f70713fe4055923d0a29d4a82c09
Source dataset
uspto-grants-2013_12
Patent number
US08614218B2

Reaction notes

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