Pyridine → HCID 87205282, compound

HRID 1510087Notes

Reaction equation

HRID 1510087 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1B(O)O.[Cl:15][C:16]1[NH:17][C:18]2[C:23]([C:24]=1[CH:25]=[O:26])=[CH:22][CH:21]=[CH:20][CH:19]=2.N1C=CC=CC=1.C(N(CC)CC)C>C(Cl)Cl.O.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[Cl:15][C:16]1[N:17]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[O:5][CH2:4][CH2:3][O:2][CH3:1])[C:18]2[C:23]([C:24]=1[CH:25]=[O:26])=[CH:22][CH:21]=[CH:20][CH:19]=2

Participants

8

Reactant 4

HCID 1049PyridineHCID 8471TriethylamineHCID 3147912-chloro-1H-indole-3-carbaldehydeHCID 18683611[2-(2-Methoxyethoxy)phenyl]boronic acid

Product 1

HCID 87205282HCID 87205282, compoundYield 6.6%

Reagents, catalysts & solvents 3

HCID 8895Cupric acetateCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a suspension of 500 mg pulverized molecular sieves (4 Å), the compound of step 2 (761 mg, 3.88 mmol), 2-chloro-1H-indole-3-carbaldehyde (465 mg, 2.59 mmol) and copper(II) acetate (940 mg, 5.18 mmol) in DCM (20 ml) was added pyridine (0.42 ml, 5.18 mmol) and triethylamine (0.72 ml, 5.18 mmol). The reaction mixture was stirred at room temperature for one week. The mixture was diluted with water and extracted with DCM. The organic layer was separated, dried over sodium sulfate, filtered and evaporated under reduced pressure. The residue was purified by preparative HPLC. The eluate was lyophilized overnight to give 56 mg of the title compound.

Workup

  1. additionTo a suspension of 500 mg
  2. extractionextracted with DCM
  3. customThe organic layer was separated
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-2cb8d19f4ae2445bbd0e7e436a76d21c
Source dataset
uspto-grants-2012_07
Patent number
US08211885B2

Reaction notes

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