Triphenylphosphine → 6-Chloro-2-iodo-3-(2-(thiophen-3-yl)ethoxy)pyridine

HRID 1190265Notes

Reaction equation

HRID 1190265 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([I:8])[C:5]([OH:9])=[CH:4][CH:3]=1.[S:10]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16]O)=[CH:11]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>O1CCCC1>[Cl:1][C:2]1[N:7]=[C:6]([I:8])[C:5]([O:9][CH2:16][CH2:15][C:12]2[CH:13]=[CH:14][S:10][CH:11]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 83731Thiophene-3-ethanolHCID 234331586-Chloro-2-iodo-3-hydroxypyridine

Product 1

HCID 582038866-Chloro-2-iodo-3-(2-(thiophen-3-yl)ethoxy)pyridineYield 58%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution 6-chloro-2-iodopyridin-3-ol (6.75 g, 26.4 mmol), 2-(3-thienyl)ethanol (3.79 mL, 34.4 mmol), and triphenylphosphine (9.01 g, 34.4 mmol) in tetrahydrofuran (140 mL) was added diisopropyl azodicarboxylate (6.76 mL, 34.4 mmol) dropwise. The reaction mixture was stirred at room temperature overnight. The reaction mixture was concentrated and purified by column on silica gel (eluted at EtOAc/Hexanes=1:20) to give 5.5 g of 6-chloro-2-iodo-3-(2-(thiophen-3-yl)ethoxy)pyridine. Yield: 58%. 1H NMR (DMSO, 400 MHz): δ7.50-7.43 (m, 3H), 7.34 (d, J=1.6 Hz, 1H), 7.17 (d, J=4.8 Hz, 1H), 4.29 (t, J=6.4 Hz, 2H), 3.10 (t, J=6.4 Hz, 2H). LC-MS (ESI): m/z=366 [M+H]

Workup

  1. concentrationThe reaction mixture was concentrated
  2. custompurified by column on silica gel (eluted at EtOAc/Hexanes=1:20)

Sources & evidence

ORD record
ord-55e95c1615ad4f3b8f1cd0ac711373a0
Source dataset
uspto-grants-2014_03
Patent number
US08673952B2

Reaction notes

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