Trimethyl((tributylstannyl)ethynyl)silane → HCID 86630695, compound

HRID 1851220Notes

Reaction equation

HRID 1851220 reaction equation
Br[C:2]1[N:24]=[C:5]2[N:6]=[C:7]([C:16]3[CH:23]=[CH:22][C:19]([CH:20]=[O:21])=[CH:18][CH:17]=3)[C:8]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)=[CH:9][N:4]2[N:3]=1.[CH3:25][Si:26]([CH3:43])([CH3:42])[C:27]#[C:28][Sn](CCCC)(CCCC)CCCC>C1(C)C=CC=CC=1.O.ClCCl.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:10]1([C:8]2[C:7]([C:16]3[CH:23]=[CH:22][C:19]([CH:20]=[O:21])=[CH:18][CH:17]=3)=[N:6][C:5]3[N:4]([N:3]=[C:2]([C:28]#[C:27][Si:26]([CH3:43])([CH3:42])[CH3:25])[N:24]=3)[CH:9]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

7

Reactant 2

HCID 639663Trimethyl((tributylstannyl)ethynyl)silaneHCID 86630694HCID 86630694, compound

Product 1

HCID 86630695HCID 86630695, compound

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

300 mg 4-(2-bromo-6-phenyl[1,2,4]triazolo[1,5-a]pyrimidin-5-yl)benzaldehyde (prepared as described above), 613 mg trimethyl[(tributylstannyl)ethynyl]silane and 46 mg Pd(PPh3)4 were suspended in 12 mL toluene under a nitrogen atmosphere. The mixture was heated (microwave irradiation) to 120° C. for 1 h. This mixture was worked up by diluting with water and extraction with dichloromethane. The 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 120° C. for 1 h
  3. dry with materialThe organic layers were dried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-05470eb4bb87437cac1c6566e1e26025
Source dataset
uspto-grants-2015_02
Patent number
US08957064B2

Reaction notes

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