Trimethyl((tributylstannyl)ethynyl)silane → HCID 86630662, compound

HRID 503735Notes

Reaction equation

HRID 503735 reaction equation
Br[C:2]1[N:6]2[CH:7]=[C:8]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:9]([C:11]3[CH:18]=[CH:17][C:14]([CH:15]=[O:16])=[CH:13][CH:12]=3)=[N:10][C:5]2=[N:4][CH:3]=1.[CH3:25][Si:26]([CH3:43])([CH3:42])[C:27]#[C:28][Sn](CCCC)(CCCC)CCCC>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:19]1([C:8]2[C:9]([C:11]3[CH:18]=[CH:17][C:14]([CH:15]=[O:16])=[CH:13][CH:12]=3)=[N:10][C:5]3[N:6]([C:2]([C:28]#[C:27][Si:26]([CH3:43])([CH3:42])[CH3:25])=[CH:3][N:4]=3)[CH:7]=2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 2

HCID 639663Trimethyl((tributylstannyl)ethynyl)silaneHCID 866306584-(3-Bromo-6-phenylimidazo[1,2-a]pyrimidin-7-yl)benzaldehyde

Product 1

HCID 86630662HCID 86630662, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
130 °C

Procedure

400 mg 4-(3-bromo-6-phenylimidazo[1,2-a]pyrimidin-7-yl)benzaldehyde (prepared as described under example 11), 820 mg trimethyl[(tributylstannyl)ethynyl]silane and 60 mg Pd(PPh3)4 are suspended in 8 ml toluene under a nitrogen atmosphere. The mixture is heated (microwave) to 130° C. for 1 h. The solvent is evaporated and the crude product is purified by column chromatography (dichloromethane/methanol)

Workup

  1. customThe solvent is evaporated
  2. customthe crude product is purified by column chromatography (dichloromethane/methanol)

Sources & evidence

ORD record
ord-195a24bfc5034691b750a2d37a1eaa5c
Source dataset
uspto-grants-2010_08
Patent number
US07776864B2

Reaction notes

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