Tributylstannane → HCID 11965056, compound

HRID 736864Notes

Reaction equation

HRID 736864 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][CH2:10][C:11]([NH2:13])=[O:12])[CH:5]=[CH:6][C:7]=1[Cl:8].[CH2:14]([SnH:18]([CH2:23][CH2:24][CH2:25][CH3:26])[CH2:19][CH2:20][CH2:21][CH3:22])[CH2:15][CH2:16][CH3:17]>O1CCCC1>[CH2:23]([Sn:18]([CH2:14][CH2:15][CH2:16][CH3:17])([CH2:19][CH2:20][CH2:21][CH3:22])/[C:10](=[CH:9]/[C:4]1[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=1)/[C:11]([NH2:13])=[O:12])[CH2:24][CH2:25][CH3:26]

Participants

4

Reactant 2

HCID 5948TributylstannaneHCID 113105043,4-Dichlorobenzenepropanamide

Product 1

HCID 11965056HCID 11965056, compoundYield 24.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

3-(3,4-dichlorophenyl)propionic acid amide (21 mg, 0.1 mmol) prepared in the same manner as in Reference Synthetic Example 8 was dissolved in tetrahydrofuran (2 ml) in nitrogen atmosphere, and under cooling with ice, tetrakistriphenylphosphine palladium(0) (5 mg, 0.004 mmol) was added, and then a tetrahydrofuran solution (0.5 ml) of tri-n-butyltin hydride (35 μl, 0.13 mmol) was dropwise added. After stirring for 30 minutes, the solution was concentrated under reduced pressure, and the residue was purified by tin-layer silica gel column chromatography (hexane:ethyl acetate=3:1) to give (E)-2-(tributylstannyl)-3-(3,4-dichlorophenyl)acrylamide (12.3 mg, 24%) as a pale yellow oily substance.

Workup

  1. additionwas added
  2. concentrationthe solution was concentrated under reduced pressure
  3. customthe residue was purified by tin-layer silica gel column chromatography (hexane:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-016000d812e145718bd331bc3255d63a
Source dataset
uspto-grants-2009_09
Patent number
US07595415B2

Reaction notes

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