Benzonitrile → HCID 71680409, compound

HRID 517646Notes

Reaction equation

HRID 517646 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[CH:4][N:3]=1.O.N1C2C(=CC=C3C=2N=CC=C3)C=CC=1.[C:24](#[N:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>[Cu]I>[I:8][C:6]1[CH:5]=[CH:4][N:3]2[N:31]=[C:24]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[N:1]=[C:2]2[CH:7]=1

Participants

5

Reactant 3

HCID 7505BenzonitrileHCID 212261,10-Phenanthroline hydrateHCID 226075514-Iodopyridin-2-amine

Product 1

HCID 71680409HCID 71680409, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)Catalyst

Conditions

Temperature
130 °C

Procedure

A mixture of 2-amino-4-iodopyridine (2.60 g, 11.8 mmol), copper (I) iodide (115 mg, 0.60 mmol), 1,10-phenanthroline monohydrate (120 mg, 0.60 mmol) and benzonitrile (33 mL) was heated in a 100 mL 4-necked flask to 130° C. During 23 h a gentle flow of O2/N2 (5:95) was bubbled through the reaction mixture (99% conversion, HPLC method see below). The dark brown suspension was then cooled to 0-5° C. and filtered. The filter cake was washed with TBME (10 mL) and dried to yield crude 7-iodo-2-phenyl-[1,2,4]triazolo[1,5-a]pyridine (2.31 g, 61%) as a green solid with 100% purity (HPLC area-%, HPLC method see below).

Workup

  1. customDuring 23 h a gentle flow of O2/N2 (5:95) was bubbled through the reaction mixture (99% conversion, HPLC method see below)
  2. temperatureThe dark brown suspension was then cooled to 0-5° C.
  3. filtrationfiltered
  4. washThe filter cake was washed with TBME (10 mL)
  5. customdried

Sources & evidence

ORD record
ord-a6f587c4c8af4bc5b0f6615b5e231126
Source dataset
uspto-grants-2015_08
Patent number
US09115130B2

Reaction notes

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