4-Iodo-2-methyl-1,3-thiazole → 2-(4-(2-Methylthiazol-4-yl)but-3-ynyl)-imidazo[1,2-a]pyridine

HRID 334571Notes

Reaction equation

HRID 334571 reaction equation
I[C:2]1[N:3]=[C:4]([CH3:7])[S:5][CH:6]=1.[CH2:8]([C:12]1[N:13]=[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][N:15]2[CH:20]=1)[CH2:9][C:10]#[CH:11]>C(N(CC)CC)C.[Cu](I)I.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>[CH3:7][C:4]1[S:5][CH:6]=[C:2]([C:11]#[C:10][CH2:9][CH2:8][C:12]2[N:13]=[C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][N:15]3[CH:20]=2)[N:3]=1

Participants

6

Reactant 2

HCID 537067904-Iodo-2-methyl-1,3-thiazoleHCID 707005722-(But-3-YN-1-YL)imidazo[1,2-A]pyridine

Product 1

HCID 665980262-(4-(2-Methylthiazol-4-yl)but-3-ynyl)-imidazo[1,2-a]pyridineYield 14%

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8471TriethylamineSolvent2×

Procedure

In a dry reaction tube containing in suspension copper iodide (6.5 mg, 0.03 mmol) and triethylamine (2.33 mL, 13.60 mmol), were added 4-iodo-2-methylthiazole (150 mg, 0.68 mmol) and Pd(PPh3)2Cl2 (39 mg, 0.03 mmol) under N2. A yellow suspension is obtained and after a few minutes of stirring at room temperature, was added a solution 2-(but-3-ynyl)-imidazo[1,2-a]pyridine (115 mg, 0.68 mmol) in triethylamine (0.5 mL) under N2. Immediately the color of the reaction turns to black. The mixture was stirred at room temperature for 4 h and 50° C. overnight under N2. Triethylamine was removed under reduce pressure. The crude product was purified by flash chromatography (Prepacked 25 g silicagel column from DCM/MeOH: 100/0 to 97/3 as eluent) to afford 25 mg of 2-(4-(2-methylthiazol-4-yl)but-3-ynyl)-imidazo[1,2-a]pyridine (Yield: 14%) as a yellow oil.

Workup

  1. customIn a dry reaction tube
  2. customA yellow suspension is obtained and after a few minutes
  3. stirringThe mixture was stirred at room temperature for 4 h and 50° C. overnight under N2
  4. customTriethylamine was removed
  5. customThe crude product was purified by flash chromatography (Prepacked 25 g silicagel column from DCM/MeOH: 100/0 to 97/3 as eluent)

Sources & evidence

ORD record
ord-990a728d1f564d16898ef089055b4197
Source dataset
uspto-grants-2014_11
Patent number
US08883826B2

Reaction notes

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