Triethylamine → HCID 178514513, compound

HRID 626673Notes

Reaction equation

HRID 626673 reaction equation
C(N(CC)CC)C.[N:8]([C:11]1[CH:16]=[CH:15][N:14]=[CH:13][C:12]=1[CH:17]=O)=[N+:9]=[N-:10].[Cl:19][C:20]1[CH:26]=[CH:25][CH:24]=[C:23]([F:27])[C:21]=1[NH2:22]>C(Cl)Cl.[Ti](Cl)(Cl)(Cl)Cl>[N:8]([C:11]1[CH:16]=[CH:15][N:14]=[CH:13][C:12]=1/[CH:17]=[N:22]/[C:21]1[C:23]([F:27])=[CH:24][CH:25]=[CH:26][C:20]=1[Cl:19])=[N+:9]=[N-:10]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 27342052-Chloro-6-fluoroanilineHCID 866970374-Azidopyridine-3-carbaldehyde

Product 1

HCID 178514513HCID 178514513, compound

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Triethylamine (7.1 mL, 51 mmol) was added to a cooled (0° C.) mixture of 4-azidopyridine-3-carbaldehyde (2.52 g, 17 mmol) and 2-chloro-6-fluoroaniline (2.47 g, 17 mmol) in DCM (60 mL) under nitrogen. Titanium tetrachloride (1 M, 10.2 mL, 10.2 mmol) was then added and the resulting mixture was stirred for 1 hour at 0° C. before warming to room temperature and stirring for a further 4 hours. The reaction mixture was concentrated under reduced pressure. The residue was suspended in toluene and filtered through a pad of Celite®. The filtrate was concentrated to dryness under reduced pressure to afford the title compound as a yellow solid. This crude material was employed in the next step without further purification or analysis.

Workup

  1. temperaturea cooled
  2. temperaturebefore warming to room temperature
  3. stirringstirring for a further 4 hours
  4. concentrationThe reaction mixture was concentrated under reduced pressure
  5. filtrationfiltered through a pad of Celite®
  6. concentrationThe filtrate was concentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-9a1f10550eab43a0996bb79675457ab6
Source dataset
uspto-grants-2016_04
Patent number
US09309240B2

Reaction notes

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