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

HRID 1190263Notes

Reaction equation

HRID 1190263 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-3yl-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-e38d26d46c204360b2ead16769568025
Source dataset
uspto-grants-2014_03
Patent number
US08673952B2

Reaction notes

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