Potassium Carbonate → 5-(Benzoxazol-2-yl)-2-(2-phenylethynyl)-1-(tetrahydropyran-4-yl)benzimidazole

HRID 74239Notes

Reaction equation

HRID 74239 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[CH:11]=[CH:12][C:13]([NH:17][CH:18]2[CH2:23][CH2:22][O:21][CH2:20][CH2:19]2)=[C:14]([CH:16]=1)[NH2:15].[C:24]1([C:30]#[C:31][CH:32]=O)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.OOS([O-])=O.[K+].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[CH:11]=[CH:12][C:13]2[N:17]([CH:18]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)[C:32]([C:31]#[C:30][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[N:15][C:14]=2[CH:16]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 75740PhenylpropynalHCID 23707502Potassium hydroxy sulfiteHCID 674988065-(Benzoxazol-2-yl)-2-(tetrahydropyran-4-yl)aminoaniline

Product 1

HCID 674981115-(Benzoxazol-2-yl)-2-(2-phenylethynyl)-1-(tetrahydropyran-4-yl)benzimidazoleYield 49%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-(benzoxazol-2-yl)-2-(tetrahydropyran-4-yl)aminoaniline (see Working Example 20-2) (38.0 mg, 0.119 mmol) in dimethylformamide (2 mL) was added phenylpropargylaldehyde (ca. 90%, 22.6 μL, 0.360 mmol) and oxone (73.2 mg, 0.119 mmol), and this was stirred at room temperature for 3 hours. After the reaction was complete, aqueous potassium carbonate solution was added, this was filtered and washed with water. The crystals obtained were purified by silica gel column chromatography to yield the title compound (20.0 mg, 49% yield) as pale yellow crystals.

Workup

  1. filtrationthis was filtered
  2. washwashed with water
  3. customThe crystals obtained
  4. customwere purified by silica gel column chromatography

Sources & evidence

ORD record
ord-a14adcba51f9401dbf1a8df79e19e20e
Source dataset
uspto-grants-2014_09
Patent number
US08829035B2

Reaction notes

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