Water → 3-(3-(Benzyloxy)-6-chloropyridin-2-yl)prop-2-yn-1-ol

HRID 1776898Notes

Reaction equation

HRID 1776898 reaction equation
[CH2:1]([O:8][C:9]1[C:10](I)=[N:11][C:12]([Cl:15])=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:17]([OH:20])[C:18]#[CH:19].O>CCN(CC)CC.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>[CH2:1]([O:8][C:9]1[C:10]([C:19]#[C:18][CH2:17][OH:20])=[N:11][C:12]([Cl:15])=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 962WaterHCID 7859Propargyl alcoholHCID 587310103-(Benzyloxy)-6-chloro-2-iodopyridine

Product 1

HCID 867282833-(3-(Benzyloxy)-6-chloropyridin-2-yl)prop-2-yn-1-olYield 91.3%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8471TriethylamineSolvent

Procedure

A mixture of compound 3-(benzyloxy)-6-chloro-2-iodopyridine (2.5 g, 7.2 mmol), prop-2-yn-1-ol (443 mg, 7.9 mmol), Pd(PPh3)2Cl2 (280 mg, 0.4 mmol) and CuI (76 mg, 0.4 mmol) in Et3N (25 mL) was stirred at room temperature for 6 hours. Water (50 mL) was added and the mixture was extracted with dichloromethane. The organic layer was washed with brine and dried over Na2SO4. After concentrated, the resulting residue was purified using column chromatography (petroleum ether:ethyl acetate=2:1) to provide the product of compound 3-(3-(benzyloxy)-6-chloropyridin-2-yl)prop-2-yn-1-ol (1.8 g, yield: 90%). 1H-NMR (CDCl3, 400 MHz) δ 7.42˜7.33 (m, 5H), 7.17 (s, 2H), 5.18 (s, 2H), 4.54 (s, 2H). MS (M+H)+: 274/276.

Workup

  1. extractionthe mixture was extracted with dichloromethane
  2. washThe organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationAfter concentrated
  5. customthe resulting residue was purified

Sources & evidence

ORD record
ord-68abb589bdcb4926ac0829e6e047f236
Source dataset
uspto-grants-2016_02
Patent number
US09265773B2

Reaction notes

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