Pyridine → HCID 58565354, compound

HRID 2175321Notes

Reaction equation

HRID 2175321 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([C:11]([N:13]([O:15][CH3:16])[CH3:14])=[O:12])[NH:6]2.[F:17][C:18]1[CH:19]=[C:20](B(O)O)[CH:21]=[CH:22][CH:23]=1.N1C=CC=CC=1>C(Cl)Cl>[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([C:11]([N:13]([O:15][CH3:16])[CH3:14])=[O:12])[N:6]2[C:22]1[CH:21]=[CH:20][CH:19]=[C:18]([F:17])[CH:23]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 27339863-Fluorophenylboronic acidHCID 23003419HCID 23003419, compound

Product 1

HCID 58565354HCID 58565354, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Activated molecular sieves (4.9 g) 4 Å were placed in an oven dried flask and cooled to room temperature under nitrogen. To the flask was charged with 4-chloro-N-methoxy-N-methyl-1H-indole-2-carboxamide (0.35 g, 1.5 mmol), (3-fluorophenyl)boronic acid (0.62 g, 4.4 mmol) and cupric acetate (0.40 g, 2.2 mmol), methylene chloride (65 mL) and then pyridine (0.47 mL, 5.9 mmol). The reaction mixture was stirred at room temperature overnight, then filtered through a pad of Celite. The filtrate was concentrated and purified on silica gel (eluting with 0-20% EtOAc in hexane) to give the desired product (0.44 g, 90%). LCMS calculated for C17H15ClFN2O2(M+H)+: m/z=333.1. Found: 333.0.

Workup

  1. customActivated molecular sieves (4.9 g) 4 Å were placed in an oven
  2. customdried flask
  3. filtrationfiltered through a pad of Celite
  4. concentrationThe filtrate was concentrated
  5. custompurified on silica gel (eluting with 0-20% EtOAc in hexane)

Sources & evidence

ORD record
ord-13722e5f59b44c659d883b45630d3cf4
Source dataset
uspto-grants-2015_06
Patent number
US09062055B2

Reaction notes

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