Triethylamine → 3-Methanesulfonyl-5-triethoxyprop-1-ynyl-pyridine

HRID 1295169Notes

Reaction equation

HRID 1295169 reaction equation
Br[C:2]1[CH:3]=[N:4][CH:5]=[C:6]([S:8]([CH3:11])(=[O:10])=[O:9])[CH:7]=1.[CH2:12]([O:14][C:15]([O:21][CH2:22][CH3:23])([O:18][CH2:19][CH3:20])[C:16]#[CH:17])[CH3:13].C(N(CC)CC)C>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.[Cu]I.ClCCl>[CH3:11][S:8]([C:6]1[CH:5]=[N:4][CH:3]=[C:2]([C:17]#[C:16][C:15]([O:18][CH2:19][CH3:20])([O:14][CH2:12][CH3:13])[O:21][CH2:22][CH3:23])[CH:7]=1)(=[O:10])=[O:9]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 109209723,3,3-Triethoxyprop-1-yneHCID 223919813-Bromo-5-(methylsulfonyl)pyridine

Product 1

HCID 225703163-Methanesulfonyl-5-triethoxyprop-1-ynyl-pyridineYield 87.3%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of 3-bromo-5-methanesulfonyl-pyridine (1.00 g, 4.20 mmol), 3,3,3-triethoxypropyne (1.75 g, 9.4 mmol), dichlorobis(triphenylphospine)palladium(II) (0.15 g, 0.21, mmol), copper(I)iodide (0.08 g, 0.42 mmol), triethylamine (1.80 mL, 12.7 mmol) and dichloromethane (40 mL) was heated at reflux for 48 h. The mixture was cooled to room temperature and the solvent was removed under reduced pressure. The crude product was chromatographed on silica (30% ethyl acetate/hexanes) to give the title compound (1.2 g, 87% yield) as yellow solid. 1H NMR (CDCl3) δ 9.08(d, 1H, J=2.4 Hz), 8.91 (d, 1H J=2.0), 8.28 (t, 1H, J=2.0 Hz), 3.75 (q, 6H, J=7.2), 3.13 (s, 3H), 1.29 (t, 9H, J=7.2).

Workup

  1. temperatureat reflux for 48 h
  2. customthe solvent was removed under reduced pressure
  3. customThe crude product was chromatographed on silica (30% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-33c8604a71804e5e9b85671f35e2f6e8
Source dataset
uspto-grants-2007_07
Patent number
US07241789B2

Reaction notes

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