Pyridine → HCID 58565348, compound

HRID 2175325Notes

Reaction equation

HRID 2175325 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 46%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Activated molecular sieves (6.0 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-indole-2-carboxamide (0.45 g, 2.2 mmol), (3-fluorophenyl)boronic acid (0.94 g, 6.7 mmol), cupric acetate (0.60 g, 3.3 mmol), and methylene chloride (80 mL) and then pyridine (0.72 mL, 8.9 mmol). The reaction mixture was stirred at room temperature over weekend, then filtered through a pad of Celite. The filtrate was concentrated and purified on silica gel (eluting with 0-25% EtOAc in hexane) to give the title compound (0.30 g, 46%). LCMS calculated for C17H16FN2O2(M+H)+: m/z=299.1. Found: 299.0.

Workup

  1. customActivated molecular sieves (6.0 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 0-25% EtOAc in hexane)

Sources & evidence

ORD record
ord-0b90f261049c4840b09469fd30752940
Source dataset
uspto-grants-2015_06
Patent number
US09062055B2

Reaction notes

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