Propargyl alcohol → HCID 12181442, compound

HRID 50573Notes

Reaction equation

HRID 50573 reaction equation
Br[C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1.[CH2:8]([OH:11])[C:9]#[CH:10].C(N(C(C)C)CC)(C)C.C(P(C(C)(C)C)C(C)(C)C)(C)(C)C>C1COCC1.[Cu](I)I>[N:4]1[CH:5]=[CH:6][CH:7]=[C:2]([C:10]#[C:9][CH2:8][OH:11])[CH:3]=1

Participants

7

Reactant 4

HCID 7859Propargyl alcoholHCID 122863-BromopyridineHCID 81531DiisopropylethylamineHCID 83681Tris(1,1-dimethylethyl)phosphine

Product 1

HCID 12181442HCID 12181442, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-bromopyridine (2.0 g, 12.6 mmol), propargyl alcohol (1.1 mL, 19 mmol), diisopropylethylamine (3.2 mL, 23 mmol), copper iodide (133 mg, 0.7 mmol) and tri-(t-butyl)phosphine (286 mg, 1.4 mmol) in degassed THF (10 mL) was treated with Pd(CH3CN)2Cl2 (181 mg, 0.7 mmol) at 25° C. under N2. After 18 h, the reaction mixture was filtered through celite, washed with ethyl acetate (2×100 mL), and concentrated in vacuo. Purification by flash chromatography (EtOAc) afforded the title compound (1.33 g, 80%) as a yellow oil. MS 134 (M+H)+.

Workup

  1. filtrationthe reaction mixture was filtered through celite
  2. washwashed with ethyl acetate (2×100 mL)
  3. concentrationconcentrated in vacuo
  4. customPurification by flash chromatography (EtOAc)

Sources & evidence

ORD record
ord-d8f36336b69b40adbd809d567cbc285f
Source dataset
uspto-grants-2004_03
Patent number
US06713455B2

Reaction notes

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