HCID 59327108, compound → HCID 59326867, compound

HRID 1880072Notes

Reaction equation

HRID 1880072 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[NH:23][C:24]5[C:25]([N:30]=4)=[N:26][CH:27]=[CH:28][CH:29]=5)=[O:21])=[CH:16][CH:15]=3)=[N:9][CH:10]=[CH:11][CH:12]=2)[CH2:3][CH2:2]1>C1COCC1.[OH-].[Pd+2].[OH-]>[NH:23]1[C:24]2[C:25](=[N:26][CH:27]=[CH:28][CH:29]=2)[N:30]=[C:22]1[CH:20]([C:17]1[CH:18]=[CH:19][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:15][CH:16]=1)[OH:21]

Participants

4

Reactant 1

HCID 59327108HCID 59327108, compound

Product 1

HCID 59326867HCID 59326867, compound

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a round bottomed flask was added (4-(3-(3,6-dihydro-2H-pyran-4-yl)pyridin-2-yloxy)phenyl)(1H-imidazo[4,5-b]pyridin-2-yl)methanone (0.3642 g, 0.914 mmol) in THF (3.05 mL). Palladium hydroxide (0.032 g, 0.046 mmol) was added. The round bottomed flask was flushed with N2(g) followed by vacuum repeating the process three times. A balloon of H2(g) was then added to the reaction. Upon completion, reaction was filtered. The crude product was adsorbed onto a plug of silica gel and chromatographed through a Biotage pre-packed silica gel column (40S), eluting with a gradient of 0.5% to 10% MeOH in DCM, to provide (1H-imidazo[4,5-b]pyridin-2-yl)(4-(3-(tetrahydro-2H-pyran-4-yl)pyridin-2-yloxy)phenyl)methanol. MS (ESI, pos. ion) m/z: 403.0 (M+1).

Workup

  1. customThe round bottomed flask was flushed with N2(g)
  2. additionA balloon of H2(g) was then added to the reaction
  3. customUpon completion, reaction
  4. filtrationwas filtered
  5. customchromatographed through a Biotage pre-packed silica gel column (40S)
  6. washeluting with a gradient of 0.5% to 10% MeOH in DCM

Sources & evidence

ORD record
ord-f6e0e552b95143c6bd17a417bafbd9af
Source dataset
uspto-grants-2012_11
Patent number
US08318718B2

Reaction notes

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