Trimethyl((tributylstannyl)ethynyl)silane → HCID 19371485, compound

HRID 129413Notes

Reaction equation

HRID 129413 reaction equation
Br[C:2]1[C:3]([F:27])=[C:4]([F:26])[CH:5]=[C:6]2[C:11]=1[N:10]([C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][C:13]=1[F:19])[CH:9]=[C:8]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:7]2=[O:25].C([Sn]([C:41]#[C:42][Si:43]([CH3:46])([CH3:45])[CH3:44])(CCCC)CCCC)CCC>C1(C)C=CC=CC=1.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[F:19][C:13]1[CH:14]=[C:15]([F:18])[CH:16]=[CH:17][C:12]=1[N:10]1[C:11]2[C:6](=[CH:5][C:4]([F:26])=[C:3]([F:27])[C:2]=2[C:41]#[C:42][Si:43]([CH3:46])([CH3:45])[CH3:44])[C:7](=[O:25])[C:8]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:9]1

Participants

5

Reactant 2

HCID 639663Trimethyl((tributylstannyl)ethynyl)silaneHCID 19371456HCID 19371456, compound

Product 1

HCID 19371485HCID 19371485, compoundYield 69%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 1140TolueneSolvent

Procedure

6.7 g of ethyl 8-bromo-1-(2,4-difluorophenyl)-6,7-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylate (Example Z20), 10.8 g of tributylstannyl-trimethylsilyl-acetylene and 0.87 g of tetrakis(triphenylphosphine)-palladium(0) are refluxed for 24 hours in 50 ml of absolute toluene under a nitrogen atmosphere. The product crystallises from the reaction mixture at -18° C. 4.8 g of ethyl 1-(2,4-difluorophenyl)-6,7-difluoro-1,4-dihydro-8-(trimethylsilylethinyl)-4-oxo-3-quinolinecarboxylate are obtained (69% of theory).

Workup

  1. customThe product crystallises from the reaction mixture at -18° C

Sources & evidence

ORD record
ord-263260b73ed84031a68f3ec5d6625946
Source dataset
uspto-grants-1995_11
Patent number
US05468742

Reaction notes

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