Tributyl(prop-1-yn-1-yl)stannane → (2-Chloro-phenyl)-(2-prop-1-ynyl-pyridin-3-yl)-methanone

HRID 2251972

Reaction equation

HRID 2251972 reaction equation
Br[C:2]1[C:7]([C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[Cl:16])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[CH2:17]([Sn](CCCC)(CCCC)C#CC)[CH2:18][CH2:19]C>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>[Cl:16][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=1[C:8]([C:7]1[C:2]([C:17]#[C:18][CH3:19])=[N:3][CH:4]=[CH:5][CH:6]=1)=[O:9]

Participants

5

Reactant 2

HCID 2733165Tributyl(prop-1-yn-1-yl)stannaneHCID 85882881(2-Bromopyridin-3-yl)-(2-chlorophenyl)methanone

Product 1

HCID 69155063(2-Chloro-phenyl)-(2-prop-1-ynyl-pyridin-3-yl)-methanone

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

Dissolve (2-bromo-pyridin-3-yl)-(2-chloro-phenyl)-methanone (18.0 g, 60.8 mmol) in toluene (600 mL) and purge the solution with nitrogen. After 10 minutes., add tributyl(1-propynyl)tin (22.2 mL, 72.9 mmol) followed by tetrakis(triphenylphosphine)palladium (2.10 g, 1.82 mmol) and heat the mixture to reflux temperature. After 2 hours, cool the mixture to room temperature and concentrate. Purification by flash chromatography on silica gel eluting with hexanes:ethyl acetate (5:1 to 2:1) gives the title compound: m.p.=45-49° C.; mass spectrum (m/e): 256 (M+H+); 1H NMR (CDCl3) δ 8.67-8.68 (m, 1H), 7.95-7.98 (m, 1H), 7.32-7.55 (m, 5H), 1.74 (s, 3H); HPLC 98.4%; TLC (Silica, 2:1 Hexanes:Ethyl Acetate) Rf 0.20.

Workup

  1. custompurge the solution with nitrogen
  2. temperatureheat the mixture
  3. temperatureto reflux temperature
  4. waitAfter 2 hours
  5. concentrationconcentrate
  6. customPurification by flash chromatography on silica gel eluting with hexanes:ethyl acetate (5:1 to 2:1)

Sources & evidence

ORD record
ord-8d9b76c71d4b474f81ee3ccd54c1ea02
Source dataset
uspto-grants-2008_01
Patent number
US07320994B2

Linked notes

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