Pyridine → HCID 58565337, compound

HRID 2175314Notes

Reaction equation

HRID 2175314 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[C:7]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[NH:8]2)=[CH:4][CH:3]=1.[F:16][C:17]1[CH:18]=[C:19](B(O)O)[CH:20]=[CH:21][CH:22]=1.N1C=CC=CC=1>C([O-])(=O)C.[Cu+2].C([O-])(=O)C.C(Cl)Cl>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[C:7]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[N:8]2[C:21]2[CH:20]=[CH:19][CH:18]=[C:17]([F:16])[CH:22]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 27339863-Fluorophenylboronic acidHCID 7015027Ethyl 6-chloroindole-2-carboxylate

Product 1

HCID 58565337HCID 58565337, compoundYield 84.3%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

Activated molecular sieves (8.9 g) 4 Å were placed in an oven dried round bottom flask and cooled to room temperature under nitrogen. Ethyl 6-chloro-1H-indole-2-carboxylate (from AsymChem, 0.500 g, 2.24 mmol), (3-fluorophenyl)boronic acid (0.938 g, 6.71 mmol), copper acetate (0.40 g, 3.3 mmol), methylene chloride (80 mL) was added to the flask, followed by pyridine (0.723 mL, 8.94 mmol). The reaction mixture was stirred at room temperature for 2 days, and then filtered through Celite. The filtrate was concentrated under reduced pressure. The resultant residue was purified by chromatography on silica gel (eluting with 0 to 50% EtOAc in hexane) to give the desired product (0.60 g). LCMS calculated for C17H14ClFNO2(M+H)+: m/z=318.1. Found: 318.1.

Workup

  1. customActivated molecular sieves (8.9 g) 4 Å were placed in an oven
  2. customdried round bottom flask
  3. filtrationfiltered through Celite
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customThe resultant residue was purified by chromatography on silica gel (eluting with 0 to 50% EtOAc in hexane)

Sources & evidence

ORD record
ord-faac5500904c4a2e8293a6a39d414f7a
Source dataset
uspto-grants-2015_06
Patent number
US09062055B2

Reaction notes

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