Triethylamine → (2R)-4-(7-Chlorothieno[3,2-b]pyridin-6-yl)but-3-yn-2-ol

HRID 712014Notes

Reaction equation

HRID 712014 reaction equation
[Cl:1][C:2]1[C:7](I)=[CH:6][N:5]=[C:4]2[CH:9]=[CH:10][S:11][C:3]=12.[CH3:12][C@@H:13]([OH:16])[C:14]#[CH:15].C(N(CC)CC)C>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>[Cl:1][C:2]1[C:7]([C:15]#[C:14][C@H:13]([OH:16])[CH3:12])=[CH:6][N:5]=[C:4]2[CH:9]=[CH:10][S:11][C:3]=12

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 638102(2R)-but-3-yn-2-olHCID 867174727-Chloro-6-iodothieno[3,2-b]pyridine

Product 1

HCID 86717473(2R)-4-(7-Chlorothieno[3,2-b]pyridin-6-yl)but-3-yn-2-ol

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalyst

Procedure

A mixture of 7-chloro-6-iodothieno[3,2-b]pyridine (0.46 g, 1.6 mmol), bis(triphenylphosphine)palladium(II) chloride (0.11 g, 0.16 mmol) and copper(I) iodide (30 mg, 0.16 mmol) was purged with N2. (2R)-but-3-yn-2-ol (0.13 g, 1.9 mmol) and triethylamine (4.5 mL, 33 mmol) was added via syringe. The reaction mixture was heated at reflux for 2 h. The mixture was concentrated under reduced pressure, and the resultant residue was purified on silica gel (eluting with 0-85% EtOAc/hexanes) to give the desired product. LCMS calculated for C11H9ClNOS (M+H)+: m/z=238.0. Found: 238.0.

Workup

  1. customwas purged with N2
  2. temperatureThe reaction mixture was heated
  3. temperatureat reflux for 2 h
  4. concentrationThe mixture was concentrated under reduced pressure
  5. customthe resultant residue was purified on silica gel (eluting with 0-85% EtOAc/hexanes)

Sources & evidence

ORD record
ord-69d6482521924856af8a470b4a6f4f35
Source dataset
uspto-grants-2015_11
Patent number
US09181271B2

Reaction notes

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