Pyridine → HCID 58565377, compound

HRID 2175348Notes

Reaction equation

HRID 2175348 reaction equation
[C:1]([C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[NH:5][C:4]=1[C:12]([O:14][CH3:15])=[O:13])#[N:2].[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>[C:1]([C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]([C:21]2[CH:20]=[CH:19][CH:18]=[C:17]([F:16])[CH:22]=2)[C:4]=1[C:12]([O:14][CH3:15])=[O:13])#[N:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 27339863-Fluorophenylboronic acidHCID 13442948HCID 13442948, compound

Product 1

HCID 58565377HCID 58565377, compoundYield 60.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Activated molecular sieves (6.0 g, 27 mmol) 4 Å were placed in an oven dried flask and cooled to room temperature under nitrogen. To the flask was charged with methyl 3-cyano-1H-indole-2-carboxylate (0.45 g, 2.2 mmol), (3-fluorophenyl)boronic acid (0.94 g, 6.7 mmol), cupric acetate (0.61 g, 3.4 mmol), methylene chloride (43 mL) and pyridine (0.73 mL, 9.0 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 0-60% EtOAc/hexane) to give the desired product (0.39 g, 59%). LCMS calculated for C17H12FN2O2(M+H)+: m/z=295.1. Found: 295.0.

Workup

  1. customActivated molecular sieves (6.0 g, 27 mmol) 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 0-60% EtOAc/hexane)

Sources & evidence

ORD record
ord-aaab3deacf12438da4591d1cfb7fd0fd
Source dataset
uspto-grants-2015_06
Patent number
US09062055B2

Reaction notes

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