Triethylamine → HCID 178510122, compound

HRID 626781Notes

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

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 4-azido-5-fluoro-3-pyridinecarboxaldehyde (1.0 g, 6.02 mmol) and 2-amino-3-chloro-5-fluorobenzonitrile (1.03 g, 6.02 mmol) in anhydrous DCM (20 mL) was cooled in an icebath and triethylamine (2.52 mL, 18.07 mmol) was added, followed by titanium (IV) chloride (1 N in DCM, 3.6 mL, 3.6 mmol). The reaction mixture was stirred at 0° C. for 3 hours and then at room temperature overnight. The resultant mixture was concentrated under reduced pressure and the residue was suspended in ethyl acetate and filtered through a pad of Celite®. The filtrate was concentrated under reduced pressure to afford the title compound as a pale brown solid (1.67 g, 89% yield), which was used directly in the next step without purification. LCMS (Method C): RT=3.74 min, m/z: 291 [M+H+−N2].

Workup

additionwas added
customat room temperature
customovernight
concentrationThe resultant mixture was concentrated under reduced pressure
filtrationfiltered through a pad of Celite®
concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record: ord-200e3b0b2c2e43eb858db134238757f6
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09309240B2

Reaction notes

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