Pyridine → 1-(3-Fluorophenyl)-N-methoxy-N,3-dimethyl-1H-indole-2-carboxamide

HRID 2175344Notes

Reaction equation

HRID 2175344 reaction equation
[CH3:1][O:2][N:3]([CH3:16])[C:4]([C:6]1[NH:7][C:8]2[C:13]([C:14]=1[CH3:15])=[CH:12][CH:11]=[CH:10][CH:9]=2)=[O:5].[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>[F:17][C:18]1[CH:23]=[C:22]([N:7]2[C:8]3[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=3)[C:14]([CH3:15])=[C:6]2[C:4]([N:3]([O:2][CH3:1])[CH3:16])=[O:5])[CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 27339863-Fluorophenylboronic acidHCID 86660482N-Methoxy-N,3-dimethyl-1H-indole-2-carboxamide

Product 1

HCID 585653381-(3-Fluorophenyl)-N-methoxy-N,3-dimethyl-1H-indole-2-carboxamideYield 12.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Activated molecular sieves (18 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,3-dimethyl-1H-indole-2-carboxamide (1.5 g, 6.9 mmol), (3-fluorophenyl)boronic acid (2.9 g, 21 mmol), cupric acetate (1.9 g, 10 mmol), methylene chloride (130 mL) and pyridine (2.2 mL, 27 mmol). The reaction mixture was stirred at room temperature for 2 days. 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 desired product (0.27 g, 12%). LCMS calculated for C18H18FN2O2(M+H)+: m/z=313.1. Found: 313.0.

Workup

  1. customActivated molecular sieves (18 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 0-30% EtOAc/hexane)

Sources & evidence

ORD record
ord-eef656eecd014f6d92564ee0f45bb47a
Source dataset
uspto-grants-2015_06
Patent number
US09062055B2

Reaction notes

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