5-(Benzoxazol-2-yl)-2-(furan-2-yl)-1-(tetrahydropyran-4-yl)benzimidazole → 5-(Benzoxazol-2-yl)-2-(tetrahydrofuran-2-yl)-1-(tetrahydropyran-4-yl)benzimidazole

HRID 74272Notes

Reaction equation

HRID 74272 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:29]=[CH:28][C:13]2[N:14]([CH:22]3[CH2:27][CH2:26][O:25][CH2:24][CH2:23]3)[C:15]([C:17]3[O:18][CH:19]=[CH:20][CH:21]=3)=[N:16][C:12]=2[CH:11]=1.[H][H]>CO.C(OCC)(=O)C.[C].[Pd]>[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:29]=[CH:28][C:13]2[N:14]([CH:22]3[CH2:23][CH2:24][O:25][CH2:26][CH2:27]3)[C:15]([CH:17]3[CH2:21][CH2:20][CH2:19][O:18]3)=[N:16][C:12]=2[CH:11]=1

Participants

5

Reactant 2

HCID 674982445-(Benzoxazol-2-yl)-2-(furan-2-yl)-1-(tetrahydropyran-4-yl)benzimidazoleHCID 178418361HCID 178418361, compound

Product 1

HCID 674984405-(Benzoxazol-2-yl)-2-(tetrahydrofuran-2-yl)-1-(tetrahydropyran-4-yl)benzimidazoleYield 34.5%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 21584119Ethylacetate methanolSolvent

Procedure

To a solution of 5-(benzoxazol-2-yl)-2-(furan-2-yl)-1-(tetrahydropyran-4-yl)benzimidazole (see Working Example 63) (90 mg, 0.234 mmol) in methanol/ethyl acetate (1:1, 6 mL) was added 10% palladium-carbon (20 mg), a hydrogen atmosphere was substituted in the flask, and this was stirred at room temperature for 20 hours. After the reaction was complete, this was filtered through Celite and the filtrate was concentrated. The residue obtained was purified by silica gel column chromatography to yield the title compound (31.4 mg, 34% yield) as a colorless amorphous mass.

Workup

  1. filtrationthis was filtered through Celite
  2. concentrationthe filtrate was concentrated
  3. customThe residue obtained
  4. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-7cfc2e43078a4c55b3dedb92311d9af8
Source dataset
uspto-grants-2014_09
Patent number
US08829035B2

Reaction notes

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