Water → HCID 66727833, compound

HRID 573357Notes

Reaction equation

HRID 573357 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[H-].[Na+].[F:11][CH:12]([F:27])[CH2:13][N:14]1[C:18]2=[N:19][CH:20]=[CH:21][CH:22]=[C:17]2[N:16]=[C:15]1S(C)(=O)=O.O>CN(C=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:15]2[N:14]([CH2:13][CH:12]([F:11])[F:27])[C:18]3=[N:19][CH:20]=[CH:21][CH:22]=[C:17]3[N:16]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 78084-BromophenolHCID 24758Sodium hydrideHCID 66727858HCID 66727858, compound

Product 1

HCID 66727833HCID 66727833, compoundYield 79.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 4-bromophenol (238 mg) in DMF (4 mL) was added NaH (60% in oil, 55.1 mg) at room temperature. The mixture was stirred at room temperature for 30 min and then 3-(2,2-difluoroethyl)-2-(methylsulfonyl)-3H-imidazo[4,5-b]pyridine (360 mg) was added. The mixture was exposed to microwave irradiation at 180° C. for 30 min, treated with water, and extracted with AcOEt. The organic layer was dried over MgSO4 and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (AcOEt/hexane) to give the title compound (387 mg).

Workup

  1. customirradiation at 180° C. for 30 min
  2. extractionextracted with AcOEt
  3. dry with materialThe organic layer was dried over MgSO4
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (AcOEt/hexane)

Sources & evidence

ORD record
ord-9385986cd4794f3486a3c5682a0cf8b5
Source dataset
uspto-grants-2015_05
Patent number
US09029536B2

Reaction notes

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