Stannane, tributyl(1-ethoxyethenyl)- → HCID 86710369, compound

HRID 1398377Notes

Reaction equation

HRID 1398377 reaction equation
Br[C:2]1[C:18]([O:19][CH2:20][C@@H:21]([NH:26][C:27](=[O:33])[O:28][C:29]([CH3:32])([CH3:31])[CH3:30])[CH2:22][CH:23]([CH3:25])[CH3:24])=[CH:17][C:5]2[N:6]([CH3:16])[C:7](=[O:15])[C:8]3[C:13]([C:4]=2[CH:3]=1)=[CH:12][CH:11]=[N:10][C:9]=3[CH3:14].C([Sn](CCCC)(CCCC)[C:39]([O:41][CH2:42][CH3:43])=[CH2:40])CCC>O1CCOCC1.O.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.[Fe+2]>[CH2:42]([O:41][C:39]([C:2]1[C:18]([O:19][CH2:20][C@@H:21]([NH:26][C:27](=[O:33])[O:28][C:29]([CH3:31])([CH3:32])[CH3:30])[CH2:22][CH:23]([CH3:25])[CH3:24])=[CH:17][C:5]2[N:6]([CH3:16])[C:7](=[O:15])[C:8]3[C:13]([C:4]=2[CH:3]=1)=[CH:12][CH:11]=[N:10][C:9]=3[CH3:14])=[CH2:40])[CH3:43]

Participants

7

Reactant 2

HCID 619414Stannane, tributyl(1-ethoxyethenyl)-HCID 86710370HCID 86710370, compound

Product 1

HCID 86710369HCID 86710369, compoundYield 34.2%

Reagents, catalysts & solvents 4

HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of (S)-tert-butyl (1-((9-bromo-4,6-dimethyl-5-oxo-5,6 dihydrobenzo[c][2,7]naphthyridin-8-yl)oxy)-4-methylpentan-2-yl)carbamate (500 mg, 0.964 mmol) in 1,4-dioxane (5 mL), tributyl(1-ethoxyvinyl)stannane (697 mg, 1.929 mmol), tris(dibenzylideneacetone)dipalladium (0) (88 mg, 0.096 mmol) and DPPF (53.5 mg, 0.096 mmol) were added. The reaction mixture was allowed to stir at 100° C. for 12 h. The reaction mixture was diluted with water and extracted in ethyl acetate. The organic layer was dried over sodium sulfate and concentrated which afforded (S)-tert-butyl (1-((9-(1-ethoxyvinyl)-4,6 dimethyl-5-oxo-5,6-dihydrobenzo[c][2,7]naphthyridin-8-yl)oxy)-4-methylpentan-2-yl)carbamate (0.3 g, 0.33 mmol, 34% crude yield) as brown solid which was carried on without further purification. LC/MS (ESI) m/e 510.2 [(M+H)+, calcd for C29H40N3O5, 510.3]; LC/MS retention time (Method=C): tR=2.60 min.

Workup

  1. extractionextracted in ethyl acetate
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. concentrationconcentrated which

Sources & evidence

ORD record
ord-028b3fdd99d147c89cd51304d387bdb5
Source dataset
uspto-grants-2014_12
Patent number
US08901305B2

Reaction notes

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