Triethylamine → HCID 178509437, compound

HRID 626808Notes

Reaction equation

HRID 626808 reaction equation
[N:1]([C:4]1[C:9]([F:10])=[CH:8][N:7]=[CH:6][C:5]=1[CH:11]=O)=[N+:2]=[N-:3].[NH2:13][C:14]1[C:21]([Cl:22])=[CH:20][C:19]([Br:23])=[CH:18][C:15]=1[C:16]#[N:17].C(N(CC)CC)C>C(Cl)Cl.[Ti](Cl)(Cl)(Cl)Cl>[N:1]([C:4]1[C:9]([F:10])=[CH:8][N:7]=[CH:6][C:5]=1/[CH:11]=[N:13]/[C:14]1[C:21]([Cl:22])=[CH:20][C:19]([Br:23])=[CH:18][C:15]=1[C:16]#[N:17])=[N+:2]=[N-:3]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 265983112-Amino-5-bromo-3-chlorobenzonitrileHCID 866970534-Azido-5-fluoropyridine-3-carbaldehyde

Product 1

HCID 178509437HCID 178509437, compound

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 4-azido-5-fluoropyridine-3-carbaldehyde (3.75 g, 22.6 mmol) and 2-amino-5-bromo-3-chlorobenzonitrile (5.24 g, 22.6 mmol) in DCM (75 mL) was cooled to 0° C. under an atmosphere of nitrogen. Triethylamine (9.5 mL, 68 mmol) was added, followed by titanium (IV) chloride solution (1 N in DCM, 13.6 mL, 13.6 mmol) dropwise. The reaction mixture was stirred at 0° C. for 2 hours and then allowed to reach room temperature overnight. The resultant mixture was concentrated under reduced pressure and the residue was suspended in toluene and filtered through a pad of Celite®. The filtrate was concentrated under reduced pressure to afford the title compound which was used in the next step without further purification.

Workup

  1. waitto reach room temperature overnight
  2. concentrationThe resultant mixture was concentrated under reduced pressure
  3. filtrationfiltered through a pad of Celite®
  4. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-07827ac237a346afbfbbe4a6a7fe8cb8
Source dataset
uspto-grants-2016_04
Patent number
US09309240B2

Reaction notes

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