Methyl iodide → HCID 16113489, compound

HRID 2070047Notes

Reaction equation

HRID 2070047 reaction equation
[F:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][C:21]3[CH:26]=[CH:25][N:24]=[C:23]4[NH:27][N:28]=[CH:29][C:22]=34)=[CH:16][CH:15]=2)=[O:12])=[CH:6][C:5]=1[C:30]([F:33])([F:32])[F:31].[H-].[Na+].I[CH3:37].[Cl-].[NH4+]>CN(C=O)C>[F:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]([NH:13][C:14]2[CH:15]=[CH:16][C:17]([O:20][C:21]3[CH:26]=[CH:25][N:24]=[C:23]4[N:27]([CH3:37])[N:28]=[CH:29][C:22]=34)=[CH:18][CH:19]=2)=[O:12])=[CH:6][C:5]=1[C:30]([F:33])([F:32])[F:31]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 16114436HCID 16114436, compound

Product 1

HCID 16113489HCID 16113489, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-[4-(2-Fluoroethyl)-3-(trifluoromethyl)phenyl]-3-[4-(1H-pyrazolo[3,4-b]pyridin-4-yloxy)phenyl]urea (92 mg, 0.2 mmol) was dissolved in DMF (1 mL), and sodium hydride (60%, 8 mg) was added thereto. The resulting mixture was stirred under nitrogen atmosphere at room temperature for 0.5 hours, and then iodomethane (18 μL) was added thereto. The mixture was further stirred overnight, and a saturated ammonium chloride aqueous solution was added thereto to quench the reaction. The reaction solution was extracted with ethyl acetate. The organic layer was washed with saturated brine and concentrated under reduced pressure. The residue was purified by silica-gel column chromatography (dichloromethane:methanol=20:1) to give 1-[4-(2-fluoro-ethyl)-3-trifluoromethyl-phenyl]-3-[4-(1-methyl-1H-pyrazolo[3,4-b]pyridin-4-yloxy)phenyl]urea (47 mg, 50%) as colorless crystals.

Workup

  1. waitThe mixture was further stirred overnight
  2. customto quench
  3. customthe reaction
  4. extractionThe reaction solution was extracted with ethyl acetate
  5. washThe organic layer was washed with saturated brine
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica-gel column chromatography (dichloromethane:methanol=20:1)

Sources & evidence

ORD record
ord-021d5f6a7d7443859933e1787d2bc397
Source dataset
uspto-grants-2012_10
Patent number
US08299252B2

Reaction notes

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