Tetrahydrofuran → 2-Iodo-3-(2-thiophen-3-ylethoxy)-pyridine

HRID 2385595Notes

Reaction equation

HRID 2385595 reaction equation
[I:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[CH:4][N:3]=1.[S:9]1[CH:13]=[CH:12][C:11]([CH2:14][CH2:15]O)=[CH:10]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O1CCCC1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>>[I:1][C:2]1[C:7]([O:8][CH2:15][CH2:14][C:11]2[CH:12]=[CH:13][S:9][CH:10]=2)=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

6

Reactant 5

HCID 8028TetrahydrofuranHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 83731Thiophene-3-ethanolHCID 971792-Iodopyridin-3-ol

Product 1

HCID 579003112-Iodo-3-(2-thiophen-3-ylethoxy)-pyridineYield 90%

Procedure

To a solution containing 2-iodo-3-hydroxypyridine (1.85 g, 8.37 mmol), 2-(3-thienyl)ethanol (1.20 mL, 10.9 mmol), and triphenylphosphine (2.85 g, 10.9 mmol) in tetrahydrofuran (46.2 mL, 5.70 mmol) was added diisopropyl azodicarboxylate (2.14 mL, 10.9 mmol) dropwise. The reaction mixture was stirred at room temperature for 18 h. The reaction mixture was concentrated and purified by flash chromatography EtOAc/Hex (0-100%) eluted at 30% to give 2-Iodo-3-(2-thiophen-3-yl-ethoxy)-pyridine (yield 90%). MS: (ESI+) 332.2

Workup

  1. concentrationThe reaction mixture was concentrated
  2. custompurified by flash chromatography EtOAc/Hex (0-100%)
  3. washeluted at 30%

Sources & evidence

ORD record
ord-b9099fabf2824e089cae474db0311b3e
Source dataset
uspto-grants-2012_09
Patent number
US08263633B2

Reaction notes

Loading…