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(4-(3-(3,6-dihydro-2H-pyran-4-yl)pyridin-2-yloxy)phenyl)(1-methyl-1H-benzo[d]imidazol-2-yl)methanone → (1-methyl-1H-benzo[d]imidazol-2-yl)(4-(3-(tetrahydro-2H-pyran-4-yl)pyridin-2-yloxy)phenyl)methanone

HRID 1880075
Notes
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Reaction equation

HRID 1880075 reaction equation
[O:1]1[CH2:6][CH:5]=[C:4]([C:7]2[C:8]([O:13][C:14]3[CH:19]=[CH:18][C:17]([C:20]([C:22]4[N:26]([CH3:27])[C:25]5[CH:28]=[CH:29][CH:30]=[CH:31][C:24]=5[N:23]=4)=[O:21])=[CH:16][CH:15]=3)=[N:9][CH:10]=[CH:11][CH:12]=2)[CH2:3][CH2:2]1>C1COCC1.[OH-].[OH-].[Pd+2].[O-2].[O-2].[Mn+4]>[CH3:27][N:26]1[C:25]2[CH:28]=[CH:29][CH:30]=[CH:31][C:24]=2[N:23]=[C:22]1[C:20]([C:17]1[CH:16]=[CH:15][C:14]([O:13][C:8]2[C:7]([CH:4]3[CH2:5][CH2:6][O:1][CH2:2][CH2:3]3)=[CH:12][CH:11]=[CH:10][N:9]=2)=[CH:19][CH:18]=1)=[O:21]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 1

HCID 59326995(4-(3-(3,6-dihydro-2H-pyran-4-yl)pyridin-2-yloxy)phenyl)(1-methyl-1H-benzo[d]imidazol-2-yl)methanone

Product 1

HCID 59326816(1-methyl-1H-benzo[d]imidazol-2-yl)(4-(3-(tetrahydro-2H-pyran-4-yl)pyridin-2-yloxy)phenyl)methanone

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 178418406HCID 178418406, compoundCatalyst
HCID 8028
Tetrahydrofuran
Solvent

Procedure

A solution of (4-(3-(3,6-dihydro-2H-pyran-4-yl)pyridin-2-yloxy)phenyl)(1-methyl-1H-benzo[d]imidazol-2-yl)methanone (0.120 g, 0.292 mmol) in THF (10 mL) was evacuated and treated with Pd(OH)2 (20 mg) under nitrogen. The reaction was stirred under a hydrogen atmosphere with a balloon. After 24 hours, the reaction was filtered through a small plug of celite and the filtrate was treated with manganese dioxide (0.254 g, 2.92 mmol). The reaction was stirred at 50° C. for 1 hour and filtered through celite. The filtered was reduced under vacuum. The residue was taken up in DCM and washed (2×) with an aqueous saturated solution of sodium bicarbonate, then with water and then brine. The organic layer was then dried with sodium sulfate and purified by column chromatography on silica gel using a gradient of 30 to 80% EtOAc in hexanes to give (1-methyl-1H-benzo[d]imidazol-2-yl)(4-(3-(tetrahydro-2H-pyran-4-yl)pyridin-2-yloxy)phenyl)methanone as a white solid. MS (ESI, pos. ion) m/z: 414.0. IC50 (uM) +++++.

Workup

  1. filtrationthe reaction was filtered through a small plug of celite
  2. stirringThe reaction was stirred at 50° C. for 1 hour
  3. filtrationfiltered through celite
  4. washwashed (2×) with an aqueous saturated solution of sodium bicarbonate
  5. dry with materialThe organic layer was then dried with sodium sulfate
  6. custompurified by column chromatography on silica gel using a gradient of 30 to 80% EtOAc in hexanes

Sources & evidence

ORD record
ord-ec0f2e768aa549889dd43d95569e8b9f
Source dataset
uspto-grants-2012_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08318718B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes