Trimethyl((tributylstannyl)ethynyl)silane → HCID 19371473, compound

HRID 129418Notes

Reaction equation

HRID 129418 reaction equation
Br[C:2]1[C:3]([F:21])=[C:4]([F:20])[CH:5]=[C:6]2[C:11]=1[N:10]([CH2:12][CH3:13])[CH:9]=[C:8]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:7]2=[O:19].C([Sn]([C:35]#[C:36][Si:37]([CH3:40])([CH3:39])[CH3:38])(CCCC)CCCC)CCC>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>[CH2:12]([N:10]1[C:11]2[C:6](=[CH:5][C:4]([F:20])=[C:3]([F:21])[C:2]=2[C:35]#[C:36][Si:37]([CH3:40])([CH3:39])[CH3:38])[C:7](=[O:19])[C:8]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:9]1)[CH3:13]

Participants

5

Reactant 2

HCID 639663Trimethyl((tributylstannyl)ethynyl)silaneHCID 19371446HCID 19371446, compound

Product 1

HCID 19371473HCID 19371473, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

5.4 g of ethyl 8-bromo-1-ethyl-6,7-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylate (Example Z22), 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 reaction mixture is concentrated, the residue is stirred with 100 ml of hexane, and the resulting solid is filtered off with suction and dried. 4.53 g of ethyl 1-ethyl-6,7-difluoro-1,4-dihydro-8-(trimethylsilylethinyl)-4-oxo-3-quinolinecarboxylate are obtained (80% of theory).

Workup

  1. concentrationThe reaction mixture is concentrated
  2. filtrationthe resulting solid is filtered off with suction
  3. customdried

Sources & evidence

ORD record
ord-c5e79359b82f4dff8661b0aff3a00c6a
Source dataset
uspto-grants-1995_11
Patent number
US05468742

Reaction notes

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