Triethylamine → HCID 178514512, compound

HRID 626699Notes

Reaction equation

HRID 626699 reaction equation
[N:1]([C:4]1[CH:9]=[CH:8][N:7]=[CH:6][C:5]=1[CH:10]=O)=[N+:2]=[N-:3].[Cl:12][C:13]1[CH:18]=[C:17]([F:19])[CH:16]=[C:15]([Cl:20])[C:14]=1[NH2:21].C(N(CC)CC)C>C(Cl)Cl.[Ti](Cl)(Cl)(Cl)Cl>[N:1]([C:4]1[CH:9]=[CH:8][N:7]=[CH:6][C:5]=1/[CH:10]=[N:21]/[C:14]1[C:13]([Cl:12])=[CH:18][C:17]([F:19])=[CH:16][C:15]=1[Cl:20])=[N+:2]=[N-:3]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 27740082,6-Dichloro-4-fluoroanilineHCID 866970374-Azidopyridine-3-carbaldehyde

Product 1

HCID 178514512HCID 178514512, compoundYield 99.8%

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Titanium tetrachloride (1M, 4.0 mL, 4.15 mmol) was added to a cooled (0° C.) mixture of 4-azidopyridine-3-carbaldehyde (1.0 g, 6.75 mmol), 2,6-dichloro-4-fluorophenylamine (1.22 g, 6.75 mmol) and triethylamine (2.8 mL, 20.3 mmol) in DCM (24 mL), under nitrogen. The reaction was stirred for 30 minutes at 0° C., warmed to room temperature, stirred for an additional 2 h, and concentrated under reduced pressure. The residue was dissolved in toluene and filtered though a pad of Celite®. The filtrate was concentrated to dryness under reduced pressure to afford the title compound as a yellow solid (2.09 g, quant.). This crude material was employed in the next step without further purification or analysis.

Workup

  1. temperaturea cooled
  2. temperaturewarmed to room temperature
  3. stirringstirred for an additional 2 h
  4. concentrationconcentrated under reduced pressure
  5. dissolutionThe residue was dissolved in toluene
  6. filtrationfiltered though a pad of Celite®
  7. concentrationThe filtrate was concentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-95e5fc1900274ec280eaa8e0f08f5c1a
Source dataset
uspto-grants-2016_04
Patent number
US09309240B2

Reaction notes

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