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

HRID 1915601Notes

Reaction equation

HRID 1915601 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 under example 53), 613 mg trimethyl[(tributylstannyl)ethynyl]silane and 46 mg Pd(PPh3)4 are suspended in 12 ml toluene under a nitrogen atmosphere. The mixture is heated (microwave irradiation) to 120° C. for 1 h. This mixture is worked up by diluting with water and extraction with dichloromethane. The 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 120° C. for 1 h
  3. dry with materialThe organic layers are dried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-4fc0b088e6c34804a588c019945ec985
Source dataset
uspto-grants-2013_12
Patent number
US08614218B2

Reaction notes

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