Potassium Hydroxide → HCID 67265260, compound

HRID 1685144Notes

Reaction equation

HRID 1685144 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[NH:15][CH:16]=[C:17]([C:19]3[CH:24]=[CH:23][C:22]([F:25])=[C:21]([Cl:26])[CH:20]=3)[N:18]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[K+].Br[CH2:30][CH2:31][O:32][CH:33]1[CH2:38][CH2:37][CH2:36][CH2:35][O:34]1>CS(C)=O.CC(=O)OCC>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[N:15]([CH2:30][CH2:31][O:32][CH:33]3[CH2:38][CH2:37][CH2:36][CH2:35][O:34]3)[CH:16]=[C:17]([C:19]3[CH:24]=[CH:23][C:22]([F:25])=[C:21]([Cl:26])[CH:20]=3)[N:18]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 866212-(2-Bromoethoxy)tetrahydro-2H-pyranHCID 178451793HCID 178451793, compound

Product 1

HCID 67265260HCID 67265260, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Dissolve 4-[4-(3-chloro-4-fluoro-phenyl)-1H-imidazol-2-yl]-piperidine-1-carboxylic acid tert-butyl ester (5.29 g; 13.93 mmol); powdered KOH (111.46 mmol; 6.95 g) in DMSO (69 mL) and heat to 40° C. for 10 min. Add 2-(2-bromoethoxy)tetrahydro-2H-pyran (34.83 mmol; 5.48 mL) dropwise over 45 min, then stir for 30 min. Cool and dilute with EA and wash with 3×300 mL saturated sodium bicarbonate, brine, dry over MgSO4, filter and evaporate. Purify on 400 g silica gel with 0-10% EA/DCM to provide the title compound (6.848 g, 97%). MS (ES): m/z=508 (M+H).

Workup

  1. temperatureCool
  2. washwash with 3×300 mL saturated sodium bicarbonate, brine
  3. dry with materialdry over MgSO4
  4. filtrationfilter
  5. customevaporate
  6. customPurify on 400 g silica gel with 0-10% EA/DCM

Sources & evidence

ORD record
ord-24c35aa12c8f42f39b0534b892f594f4
Source dataset
uspto-grants-2012_04
Patent number
US08148387B2

Reaction notes

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