5-Bromo-2-iodopyridine → HCID 67228144, compound

HRID 1515862Notes

Reaction equation

HRID 1515862 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5](I)=[N:6][CH:7]=1.C([Mg]Cl)(C)C.[C:14]1([S:20]([N:23]2[C:27]3=[N:28][CH:29]=[CH:30][CH:31]=[C:26]3[CH:25]=[C:24]2[C:32](=[O:39])[CH2:33][CH:34]2[CH2:38][CH2:37][CH2:36][CH2:35]2)(=[O:22])=[O:21])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>O1CCCC1>[C:14]1([S:20]([N:23]2[C:27]3=[N:28][CH:29]=[CH:30][CH:31]=[C:26]3[CH:25]=[C:24]2[C:32]([C:5]2[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][N:6]=2)([OH:39])[CH2:33][CH:34]2[CH2:35][CH2:36][CH2:37][CH2:38]2)(=[O:21])=[O:22])[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 5936905-Bromo-2-iodopyridineHCID 67228998HCID 67228998, compoundHCID 178418918HCID 178418918, compound

Product 1

HCID 67228144HCID 67228144, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
0 °C

Procedure

To a solution of 5-bromo-2-iodopyridine (4.27 g, 15.0 mmol) in anhydrous tetrahydrofuran (60 mL) at 0° C. was added a solution of isopropylmagnesium chloride in tetrahydrofuran (2 M, 7.5 mL, 15.04 mmol) dropwise. After stirring for 30 min at 0° C., a solution of 1-(1-benzenesulfonyl-1H-pyrrolo[2,3-b]pyridin-2-yl)-2-cyclopentyl-ethanone (prepared as in Example 43, 1.38 g, 3.76 mmol) in dry tetrahydrofuran (10 mL) was added dropwise. The resulting mixture was stirred for 14 h at room temperature, quenched with a saturated sodium chloride, extracted with ethyl acetate, dried over anhydrous sodium sulfate, and concentrated in vacuo. Purification by flash column chromatography (QingDao silica gel, 200-300 mesh, 20% ethyl acetate/hexanes) afforded 1-(1-benzenesulfonyl-1H-pyrrolo[2,3-b]pyridin-2-yl)-1-(5-bromo-pyridin-2-yl)-2-cyclopentyl-ethanol (870 mg, 15%) as a light yellow solid: LC/MS m/e calcd for C25H24BrN3O3S [M+H]+ 527.46, observed 527.

Workup

  1. stirringThe resulting mixture was stirred for 14 h at room temperature
  2. customquenched with a saturated sodium chloride
  3. extractionextracted with ethyl acetate
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customPurification by flash column chromatography (QingDao silica gel, 200-300 mesh, 20% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-3f1484d9369c47b7b7dfd871291fc557
Source dataset
uspto-grants-2012_07
Patent number
US08222416B2

Reaction notes

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