Imidazole → HCID 67990244, compound

HRID 1184772Notes

Reaction equation

HRID 1184772 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH:14]2[O:23][C:17]3=[CH:18][N:19]=[C:20](Br)[CH:21]=[C:16]3[CH2:15]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH:24]1[CH:28]=[CH:27][N:26]=[CH:25]1.C(=O)([O-])[O-].[Cs+].[Cs+].N1C2C(=CC=C3C=2N=CC=C3)C=CC=1>CO.C(OCC)(=O)C.O.[Cu](I)I>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH:14]2[O:23][C:17]3=[CH:18][N:19]=[C:20]([N:24]4[CH:28]=[CH:27][N:26]=[CH:25]4)[CH:21]=[C:16]3[CH2:15]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

9

Reactant 4

HCID 795ImidazoleHCID 13181,10-PhenanthrolineHCID 10796Cesium carbonateHCID 86674903HCID 86674903, compound

Product 1

HCID 67990244HCID 67990244, compound

Reagents, catalysts & solvents 4

HCID 83717Copper iodideCatalystHCID 887MethanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 4-(5-bromo-2,3-dihydro-furo[2,3-c]pyridin-2-yl)-piperidine-1-carboxylic acid tert-butyl ester (115 mg), imidazole (41 mg), cesium carbonate (215 mg), 1,10-phenanthroline (11 mg), and copper iodide (6 mg) in methanol (2 mL) is heated in a microwave oven to 130° C. for 45 min under an argon atmosphere. After cooling to room temperature the reaction mixture is diluted with ethyl acetate and water. The organic phase is separated, washed with brine, dried over MgSO4 and concentrated in vacuo. The residue is purified by HPLC to give the title compound. LC (method 7): tR=1.16 min; Mass spectrum (ESI+): m/z=371 [M+H]+.

Workup

  1. temperatureAfter cooling to room temperature the reaction mixture
  2. customThe organic phase is separated
  3. washwashed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue is purified by HPLC

Sources & evidence

ORD record
ord-fcc9b2cd63544f42aa1f29f277cd8a51
Source dataset
uspto-grants-2014_03
Patent number
US08669271B2

Reaction notes

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