Diethyl Ether → 2-(5-ethenyl-3-pyridyloxy)-N-(4-methylpent-2-yn-4-yl)butyramide

HRID 1374922Notes

Reaction equation

HRID 1374922 reaction equation
Br[C:2]1[CH:3]=[C:4]([O:8][CH:9]([CH2:19][CH3:20])[C:10]([NH:12][C:13]([CH3:18])([CH3:17])[C:14]#[C:15][CH3:16])=[O:11])[CH:5]=[N:6][CH:7]=1.[CH2:21](C([Sn])=C(CCCC)CCCC)[CH2:22]CC.C(OCC)C>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>[CH:21]([C:2]1[CH:3]=[C:4]([O:8][CH:9]([CH2:19][CH3:20])[C:10]([NH:12][C:13]([CH3:18])([CH3:17])[C:14]#[C:15][CH3:16])=[O:11])[CH:5]=[N:6][CH:7]=1)=[CH2:22]

Participants

6

Reactant 3

HCID 3283Diethyl EtherHCID 21078374HCID 21078374, compoundHCID 53438229Tri(butyl)vinyltin

Product 1

HCID 210783972-(5-ethenyl-3-pyridyloxy)-N-(4-methylpent-2-yn-4-yl)butyramide

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 1140TolueneSolvent

Procedure

2-(5-Bromo-3-pyridyloxy)-N-(4-methylpent-2-yn-4-yl)butyramide (0.34 g), tetrakis(triphenylphosphine) palladium (0) (0.0.02 g) and tributylvinyl tin(0.38 g) in dry toluene (5 ml) were stirred and heated to reflux for 9 hours under an atmosphere of nitrogen. The mixture was cooled to ambient temperature, stored for 72 hours then evaporated under reduced pressure to give a gum that was fractionated by chromatography (silica; diethyl ether) to give the required product, 0.16 g, as a colourless gum.

Workup

  1. temperatureheated
  2. temperatureto reflux for 9 hours under an atmosphere of nitrogen
  3. customthen evaporated under reduced pressure
  4. customto give a gum that

Sources & evidence

ORD record
ord-e6c03cd31a444b4aaf4b5d9d97ec757c
Source dataset
uspto-grants-2007_01
Patent number
US07166621B2

Reaction notes

Loading…