Methyl iodide → HCID 11623273, compound

HRID 334570Notes

Reaction equation

HRID 334570 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%

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 mmol, 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, saturated solution of NaHCO3, brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customevaporated
  6. customThe crude residue was purified by flash chromatography (DCM/MeOH 99:1)

Sources & evidence

ORD record
ord-42f9a256c5404509a3f3b3f31955b431
Source dataset
uspto-grants-2014_11
Patent number
US08883826B2

Reaction notes

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