Pyridine → HCID 58565348, compound

HRID 2175332Notes

Reaction equation

HRID 2175332 reaction equation
[CH3:1][O:2][N:3]([CH3:15])[C:4]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[CH:10][CH:9]=2)=[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:7]2[C:8]3[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=3)[CH:14]=[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 11095718N-methoxy-N-methyl-1H-indole-2-carboxamide

Product 1

HCID 58565348HCID 58565348, compoundYield 37.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Activated molecular sieves (13 g) 4 Å were placed in an oven dried round bottom flask and cooled to room temperature under nitrogen. To the flask was charged with N-methoxy-N-methyl-1H-indole-2-carboxamide (0.97 g, 4.7 mmol), (3-fluorophenyl)-boronic acid (1.5 g, 11 mmol), cupric acetate (1.3 g, 7.3 mmol), methylene chloride (130 mL) and then pyridine (1.5 mL, 19 mmol). The reaction mixture was stirred at room temperature over the weekend. The mixture was filtered through a pad of Celite. The filtrate was concentrated and purified on silica gel (eluting with 0-30% EtOAc/hexane) to give the title compound (0.52 g, 37%). LCMS calculated for C17H16FN2O2(M+H)+: m/z=299.1. Found: 299.1.

Workup

  1. customActivated molecular sieves (13 g) 4 Å were placed in an oven
  2. customdried round bottom flask
  3. filtrationThe mixture was filtered through a pad of Celite
  4. concentrationThe filtrate was concentrated
  5. custompurified on silica gel (eluting with 0-30% EtOAc/hexane)

Sources & evidence

ORD record
ord-48430188543a4e988e2787475bc4030f
Source dataset
uspto-grants-2015_06
Patent number
US09062055B2

Reaction notes

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