HCID 59242951, compound → 3-Bromo-2-(2-but-1-ynyl-5-chloro-phenoxymethyl)-pyridine

HRID 423211Notes

Reaction equation

HRID 423211 reaction equation
[Br:1][C:2]1[C:3]([CH2:8][O:9][C:10]2[CH:15]=[C:14]([Cl:16])[CH:13]=[CH:12][C:11]=2I)=[N:4][CH:5]=[CH:6][CH:7]=1>C(NCC)C.CCOCC.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Br:1][C:2]1[C:3]([CH2:8][O:9][C:10]2[CH:15]=[C:14]([Cl:16])[CH:13]=[CH:12][C:11]=2[C:7]#[C:2][CH2:3][CH3:8])=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 1

HCID 59242951HCID 59242951, compound

Product 1

HCID 592429473-Bromo-2-(2-but-1-ynyl-5-chloro-phenoxymethyl)-pyridineYield 147.4%

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 3283Diethyl EtherSolventHCID 8021DiethylamineSolvent

Procedure

3-Bromo-2-(5-chloro-2-iodo-phenoxymethyl)-pyridine (3.8 g, 8.9 mmol), is placed in a pressure flask, dissolved in diethylamine:acetonitrile:THF (18 mL:4 mL:4 mL), and degassed with nitrogen for 15 min. An excess of 1-butyne is bubbled through the solution followed by the addition of Cut (507 mg, 2.66 mmol), and PdCl2(PPh3)2 (623 mg, 0.888 mmol). The mixture is stirred at room temperature for 1 h. The mixture is then diluted with ether and washed with saturated aqueous ammonium chloride and brine. The organic portion is dried over MgSO4, filtered, and concentrated under reduced pressure. The residue is purified by flash chromatography (Biotage® Si65M, 30% hexane/CH2Cl2 then 20% ethyl acetate/hexane) to provide 2.3 g (75%) of the title compound as a pale orange solid. LCMS m/e 351 [M]+.

Workup

  1. customacetonitrile:THF (18 mL:4 mL:4 mL), and degassed with nitrogen for 15 min
  2. customAn excess of 1-butyne is bubbled through the solution
  3. washwashed with saturated aqueous ammonium chloride and brine
  4. dry with materialThe organic portion is dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue is purified by flash chromatography (Biotage® Si65M, 30% hexane/CH2Cl2

Sources & evidence

ORD record
ord-bfa46605881b4cc0aaae1d31521bec9a
Source dataset
uspto-grants-2012_01
Patent number
US08101760B2

Reaction notes

Loading…