Triethylamine → HCID 178514521, compound

HRID 626792Notes

Reaction equation

HRID 626792 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]=[CH:18][CH:17]=[C:16]([F:20])[C:15]=1[NH2:21].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:21]/[C:15]1[C:16]([F:20])=[CH:17][CH:18]=[CH:19][C:14]=1[Cl:13])=[N+:2]=[N-:3]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 27342052-Chloro-6-fluoroanilineHCID 866970534-Azido-5-fluoropyridine-3-carbaldehyde

Product 1

HCID 178514521HCID 178514521, compound

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 4-azido-5-fluoropyridine-3-carbaldehyde (10.0 g, 60.0 mmol) and 2-chloro-6-fluorophenylamine (8.7 g, 60.0 mmol) in DCM (200 mL) was cooled to 0° C. under an atmosphere of nitrogen. Triethylamine (25 mL, 180 mmol) was added, followed by titanium (IV) chloride solution (1 N in DCM, 36 mL, 36 mmol) dropwise. The reaction mixture was stirred at 0° C. 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 purification.

Workup

  1. concentrationThe resultant mixture was concentrated under reduced pressure
  2. filtrationfiltered through a pad of Celite®
  3. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-9563bd1afd98490eab75e2b5fe7d6d7f
Source dataset
uspto-grants-2016_04
Patent number
US09309240B2

Reaction notes

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