Triethylamine → HCID 178514519, compound

HRID 626741Notes

Reaction equation

HRID 626741 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].[Cl:13][C:14]1[CH:19]=[C:18]([F:20])[CH:17]=[C:16]([Cl:21])[C:15]=1[NH2:22].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:22]/[C:15]1[C:14]([Cl:13])=[CH:19][C:18]([F:20])=[CH:17][C:16]=1[Cl:21])=[N+:2]=[N-:3]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 27740082,6-Dichloro-4-fluoroanilineHCID 866970534-Azido-5-fluoropyridine-3-carbaldehyde

Product 1

HCID 178514519HCID 178514519, compound

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a cooled (0° C.) solution of 4-azido-5-fluoro-pyridine-3-carbaldehyde (2.44 g, 14.7 mmol), 2,6-dichloro-4-fluorophenylamine (2.65 g, 14.7 mmol) and triethylamine (6.1 mL, 44 mmol) in DCM (50 mL) was added titanium tetrachloride (1M in DCM, 8.8 mL, 8.8 mmol) dropwise. The reaction mixture was stirred at 0° C. for 1 hour, warmed to room temperature, and stirred for a further 4 hours. The mixture was concentrated under reduced pressure. The residue was dissolved in toluene and filtered through Celite®. The filtrate was concentrated under to dryness under reduced pressure to afford the title compound that was used without further purification.

Workup

  1. temperaturewarmed to room temperature
  2. stirringstirred for a further 4 hours
  3. concentrationThe mixture was concentrated under reduced pressure
  4. dissolutionThe residue was dissolved in toluene
  5. filtrationfiltered through Celite®
  6. concentrationThe filtrate was concentrated under to dryness under reduced pressure

Sources & evidence

ORD record
ord-da6f08ddb3384eeab3f246e0db6b358c
Source dataset
uspto-grants-2016_04
Patent number
US09309240B2

Reaction notes

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