Triethylamine → HCID 178509786, compound

HRID 626787Notes

Reaction equation

HRID 626787 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]([F:22])=[CH:20][CH:19]=[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]([F:22])=[CH:20][CH:19]=[CH:18][C:15]=1[C:16]#[N:17])=[N+:2]=[N-:3]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 27833922-Amino-3-fluorobenzonitrileHCID 866970534-Azido-5-fluoropyridine-3-carbaldehyde

Product 1

HCID 178509786HCID 178509786, compound

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 4-azido-5-fluoropyridine-3-carbaldehyde (3.66 g, 22.1 mmol) and 2-amino-3-fluorobenzonitrile (3.0 g, 22.05 mmol) in DCM (73 mL) was cooled to 0° C. under an atmosphere of nitrogen. Triethylamine (9.1 mL, 66.0 mmol) was added, followed by dropwise addition of titanium (IV) chloride solution (1 N in DCM, 13.15 mL, 13.15 mmol). The reaction mixture was stirred at 0° C. for 2 hours, then at room temperature overnight. The resultant mixture was concentrated under reduced pressure to afford the title compound as a beige residue (5.19 g, 83% yield). This material was used in the next step without purification. LCMS (Method C): RT=3.49 min, m/z: 257 [M−N2].

Workup

  1. customat room temperature
  2. customovernight
  3. concentrationThe resultant mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-e2f78457d27b4db08f327140143255ea
Source dataset
uspto-grants-2016_04
Patent number
US09309240B2

Reaction notes

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