Tetrahydrofuran → HCID 68996099, compound

HRID 28932Notes

Reaction equation

HRID 28932 reaction equation
[Br:1][C:2]1[C:3]([C:7]2[CH:12]=[CH:11][C:10]([NH:13][C:14]([NH:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[O:15])=[CH:9][CH:8]=2)=[N:4][NH:5][CH:6]=1.[CH3:23][C:24](C)([O-:26])[CH3:25].[K+].O1CC[CH2:31][CH2:30]1.O1CCCC1Br>CN(C)C=O>[Br:1][C:2]1[C:3]([C:7]2[CH:12]=[CH:11][C:10]([NH:13][C:14]([NH:16][C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)=[O:15])=[CH:9][CH:8]=2)=[N:4][N:5]([CH2:23][CH:24]2[CH2:25][CH2:31][CH2:30][O:26]2)[CH:6]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 130702942-BromotetrahydrofuranHCID 23665647Potassium tert-butoxideHCID 178521959HCID 178521959, compound

Product 1

HCID 68996099HCID 68996099, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of N-[4-(4-bromo-1H-pyrazol-3-yl)phenyl]-N′-phenylurea (0.28 mmol) in anhydrous N,N-dimethylformamide (6 mL) cooled to 0° C. was added 1.0M potassium tert-butoxide in tetrahydrofuran (1.12 mmol) dropwise. The reaction mixture was stirred for a further 15 minutes in the cold before dropwise addition of tetrahydrofuryl bromide (0.28 mmol). The reaction mixture was stirred at room temperature for 18 h, followed by quenching with saturated aqueous ammonium chloride (1 mL). The reaction mixture was diluted with water (3 mL) and extracted with ethyl acetate (3×5 mL). The combined organic layers were dried over magnesium sulfate and concentrated in vacuo. Gilson reverse phase HPLC afforded the title compound (53%). ESMS [M+H]+: 441.4

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 18 h
  2. customby quenching with saturated aqueous ammonium chloride (1 mL)
  3. additionThe reaction mixture was diluted with water (3 mL)
  4. extractionextracted with ethyl acetate (3×5 mL)
  5. dry with materialThe combined organic layers were dried over magnesium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-27222053011f4de199da5d330d6b767a
Source dataset
uspto-grants-2008_09
Patent number
US07419988B2

Reaction notes

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