Pyridine → HCID 58565343, compound

HRID 2175338Notes

Reaction equation

HRID 2175338 reaction equation
[CH3:1][O:2][N:3]([CH3:15])[C:4]([C:6]1[NH:14][C:9]2=[N:10][CH:11]=[CH:12][CH:13]=[C:8]2[CH:7]=1)=[O:5].[F:16][C:17]1[CH:18]=[C:19](B(O)O)[CH:20]=[CH:21][CH:22]=1.N1C=CC=CC=1>C(Cl)Cl>[F:16][C:17]1[CH:22]=[C:21]([N:14]2[C:9]3=[N:10][CH:11]=[CH:12][CH:13]=[C:8]3[CH:7]=[C:6]2[C:4]([N:3]([O:2][CH3:1])[CH3:15])=[O:5])[CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 27339863-Fluorophenylboronic acidHCID 86660481HCID 86660481, compound

Product 1

HCID 58565343HCID 58565343, compoundYield 83.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Activated molecular sieves (3.8 g) 4 Å were placed in an oven dried flask and cooled to room temperature under nitrogen. To the flask was charged with N-methoxy-N-methyl-1H-pyrrolo[2,3-b]pyridine-2-carboxamide (0.29 g, 1.4 mmol), (3-fluorophenyl)boronic acid (0.59 g, 4.2 mmol), cupric acetate (0.38 g, 2.1 mmol), methylene chloride (35 mL) and then pyridine (0.46 mL, 5.6 mmol). The reaction mixture was stirred at room temperature overnight. The mixture was filtered through a pad of Celite. The filtrate was concentrated and purified on silica gel (eluting with 0-50% EtOAc/hexane followed by 0-5% MeOH/dichloromethane) to give the desired product (0.35 g, 83%). LCMS calculated for C16H15FN3O2(M+H)+: m/z=300.1. Found: 300.0.

Workup

  1. customActivated molecular sieves (3.8 g) 4 Å were placed in an oven
  2. customdried flask
  3. filtrationThe mixture was filtered through a pad of Celite
  4. concentrationThe filtrate was concentrated
  5. custompurified on silica gel (eluting with 0-50% EtOAc/hexane followed by 0-5% MeOH/dichloromethane)

Sources & evidence

ORD record
ord-61543806a5784091bf0fa4364c60fe82
Source dataset
uspto-grants-2015_06
Patent number
US09062055B2

Reaction notes

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