3-(2-(4-((1H-Benzo[D]imidazol-2-YL)(hydroxy)methyl)phenoxy)pyridin-3-YL)cyclopent-2-enol → 3-(2-(4-((1H-Benzo[D]imidazol-2-YL)(hydroxy)methyl)phenoxy)pyridin-3-YL)cyclopentanol

HRID 410298Notes

Reaction equation

[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH:10]([OH:30])[C:11]1[CH:29]=[CH:28][C:14]([O:15][C:16]2[C:21]([C:22]3[CH2:26][CH2:25][CH:24]([OH:27])[CH:23]=3)=[CH:20][CH:19]=[CH:18][N:17]=2)=[CH:13][CH:12]=1.[H][H]>O1CCCC1.[Pd]>[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH:10]([OH:30])[C:11]1[CH:29]=[CH:28][C:14]([O:15][C:16]2[C:21]([CH:22]3[CH2:26][CH2:25][CH:24]([OH:27])[CH2:23]3)=[CH:20][CH:19]=[CH:18][N:17]=2)=[CH:13][CH:12]=1

Participants

Conditions

Temperature: 40 °C

Procedure

A solution of 3-(2-(4-((1H-benzo[d]imidazol-2-yl)(hydroxy)methyl)phenoxy)pyridin-3-yl)cyclopent-2-enol (780 mg, 1.953 mmol) in Tetrahydrofuran (50 mL) was treated with palladium, 10% wt. on activated carbon (208 mg, 0.195 mmol) under nitrogen. The reaction flask was equipped with a hydrogen balloon and cycled through vacuum-hydrogen cycles (3×). The reaction was heated to 40° C. under hydrogen. After 5 h, the reaction was cooled to 23° C., and filtered through celite. The filter cake was washed with tetrahydrofuran (200 mL), the filtrates combined and concentrated, affording the product as a white solid. MS (ESI, pos. ion) m/z: 402.1 (M+1).

Workup

temperaturethe reaction was cooled to 23° C.
filtrationfiltered through celite
washThe filter cake was washed with tetrahydrofuran (200 mL)
concentrationconcentrated

Sources & evidence

ORD record: ord-86098d7b0fd84e7e859ecfa2081ffe4a
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08759532B2

Reaction notes

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