Triethylamine → HCID 178509965, compound

HRID 626718Notes

Reaction equation

HRID 626718 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:17]([C:18]#[N:19])=[CH:16][C:15]=1[Cl:23].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:15]([Cl:23])=[CH:16][C:17]([C:18]#[N:19])=[CH:20][C:21]=1[Cl:22])=[N+:2]=[N-:3]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 5227064-Amino-3,5-dichlorobenzonitrileHCID 866970534-Azido-5-fluoropyridine-3-carbaldehyde

Product 1

HCID 178509965HCID 178509965, compound

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a cooled (0° C.) solution of 4-azido-5-fluoro-pyridine-3-carbaldehyde (2.0 g, 12.0 mmol), 4-amino-3,5-dichlorobenzonitrile (2.25 g, 12.0 mmol) and triethylamine (5.0 mL, 36.1 mmol) in DCM (48 mL) was added titanium tetrachloride (1M in DCM, 7.2 mL, 7.2 mmol) dropwise over 20 minutes. The reaction mixture was stirred for 20 minutes, warmed to room temperature, and stirred for a further 30 minutes. The resultant mixture was concentrated to dryness under reduced pressure to afford the title compound, which was used without further purification.

Workup

  1. stirringstirred for a further 30 minutes
  2. concentrationThe resultant mixture was concentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-731df257e2594d21adbbb6f29e57b504
Source dataset
uspto-grants-2016_04
Patent number
US09309240B2

Reaction notes

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