Methyl iodide → HCID 11623273, compound

HRID 422299Notes

Reaction equation

HRID 422299 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]#[C:8][CH2:9][CH2:10][C:11]1[O:12][C:13]2[C:14](=[C:16]([OH:20])[CH:17]=[CH:18][CH:19]=2)[N:15]=1.CI.[C:23]([O-])([O-])=O.[K+].[K+]>CN(C=O)C.C(Cl)Cl>[CH3:23][O:20][C:16]1[C:14]2[N:15]=[C:11]([CH2:10][CH2:9][C:8]#[C:7][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=3)[O:12][C:13]=2[CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 11680534HCID 11680534, compound

Product 1

HCID 11623273HCID 11623273, compoundYield 47.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-(4-(pyridin-2-yl)but-3-ynyl)benzo[d]oxazol-4-ol (20 mg, 76 μmol, Example 70), methyl iodide (57 μL, 114 μmol) and K2CO3 (18 mg, 130 μmol) in DMF (2 mL) was stirred under reflux for 3 h. The reaction mixture was then allowed to cool to room temperature and was dissolved in DCM. The organic phase was washed with water, HCl 1N; saturated solution of NaHCO3, brine, dried over MgSO4, filtered and evaporated. The crude residue was purified by flash chromatography (DCM/MeOH 99:1) to yield 10 mg (36 μmol, 47%) of 4-methoxy-2-(4-(pyridin-2-yl)but-3-ynyl)benzo[d]oxazole as a brown solid.

Workup

  1. temperatureunder reflux for 3 h
  2. washThe organic phase was washed with water, HCl 1N
  3. dry with materialsaturated solution of NaHCO3, brine, dried over MgSO4
  4. filtrationfiltered
  5. customevaporated
  6. customThe crude residue was purified by flash chromatography (DCM/MeOH 99:1)

Sources & evidence

ORD record
ord-d85be23755e84283b0da0505076ac68c
Source dataset
uspto-grants-2012_01
Patent number
US08101637B2

Reaction notes

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