Water → 1-benzenesulfonyl-5-methylthio-2-(2-pyrimidinyl)-1H-pyrrolo[2,3-b]pyridine

HRID 1432219Notes

Reaction equation

HRID 1432219 reaction equation
[C:1]1([S:7]([NH:10][C:11]2[C:16](I)=[CH:15][C:14]([S:18][CH3:19])=[CH:13][N:12]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:20]([C:22]1[N:27]=[CH:26][CH:25]=[CH:24][N:23]=1)#[CH:21].O>C(N(CC)CC)C>[C:1]1([S:7]([N:10]2[C:11]3=[N:12][CH:13]=[C:14]([S:18][CH3:19])[CH:15]=[C:16]3[CH:21]=[C:20]2[C:22]2[N:27]=[CH:26][CH:25]=[CH:24][N:23]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 962WaterHCID 124412972-EthynylpyrimidineHCID 154868512-Benzenesulfonylamino-3-iodo-5-methylthiopyridine

Product 1

HCID 225044171-benzenesulfonyl-5-methylthio-2-(2-pyrimidinyl)-1H-pyrrolo[2,3-b]pyridineYield 84%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Conditions

Temperature
100 °C

Procedure

A suspension of 2-benzenesulfonylamino-5-methylthio-3-iodo-pyridine (1.53 g), 2-ethynylpyrimidine (768 mg), bistriphenylphosphine palladium dichloride (259 mg) and cuprous iodide (70.3 mg) in triethylamine (37 ml) was stirred in a sealed tube at 100° C. for 1.5 hours. After cooling, the reaction solution was poured into water, extracted with chloroform, dried over, anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The resulting residue was separated using silica gel column chromatography (hexane:ethyl acetate=1:1) to obtain 1.21 g of the desired product as a white crystal.

Workup

  1. temperatureAfter cooling
  2. extractionextracted with chloroform
  3. dry with materialdried over, anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was separated

Sources & evidence

ORD record
ord-df2b83b0bb6a4fdcbf1eda579c951a25
Source dataset
uspto-grants-2009_11
Patent number
US07612070B2

Reaction notes

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