4-Cyanobenzoyl chloride → HCID 59556569, compound

HRID 1172967Notes

Reaction equation

HRID 1172967 reaction equation
[C:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7](Cl)=[O:8])=[CH:5][CH:4]=1)#[N:2].[Br:12][C:13]1[CH:14]=[C:15]([CH:20]=[CH:21][C:22]=1[O:23][CH:24]([CH3:26])[CH3:25])/[C:16](=[N:18]/O)/[NH2:17]>N1C=CC=CC=1>[Br:12][C:13]1[CH:14]=[C:15]([C:16]2[N:18]=[C:7]([C:6]3[CH:10]=[CH:11][C:3]([C:1]#[N:2])=[CH:4][CH:5]=3)[O:8][N:17]=2)[CH:20]=[CH:21][C:22]=1[O:23][CH:24]([CH3:26])[CH3:25]

Participants

4

Reactant 2

HCID 801724-Cyanobenzoyl chlorideHCID 59556753HCID 59556753, compound

Product 1

HCID 59556569HCID 59556569, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
200 °C

Procedure

A 25 mL microwave vial equipped with a stirring bar was charged with 4-cyanobenzoyl chloride (0.4 g, 2.416 mmol), (Z)-3-bromo-N′-hydroxy-4-isopropoxybenzimidamide (0.5 g, 1.831 mmol) and pyridine (15 ml) to give an orange solution. The vessel was capped and the reaction heated at 200° C. for 20 min under microwave irradiation (Biotage Optimizer, 300 W). The solution was cooled, the reaction mixture was partitioned between aqueous HCl (10%, 150 mL) and DCM (40 mL) mixture, the DCM layer was drained, and the aqueous layer was extracted by DCM (2×20 mL). The combined DCM layers were washed by water (2×20 mL) and concentrated to afford white solid, which was purified via silica gel chromatography (40 g, 40% EtOAc:Heptane) to afford 4-(3-(3-bromo-4-isopropoxyphenyl)-1,2,4-oxadiazol-5-yl)benzonitrile (0.638 g, 1.660 mmol, 91% yield) as white solid. LC/MS (Method c) Rt=3.17 min.; MS m/z: 386.19 (M+H)+. 1H NMR (400 MHz, Solvent d-DMSO) ppm 8.40-8.32 (m, 2H), 8.23 (d, J=2.13 Hz, 1H), 8.14 (dd, J=8.14, 0.61 Hz, 2H), 8.05 (dd, J=8.65, 2.15 Hz, 1H), 7.36 (d, J=9.12 Hz, 1H), 4.89-4.77 (m, 1H), 1.35 (d, J=6.03 Hz, 6H).

Workup

  1. customA 25 mL microwave vial equipped with a stirring bar
  2. customto give an orange solution
  3. customThe vessel was capped
  4. temperatureThe solution was cooled
  5. customthe reaction mixture was partitioned between aqueous HCl (10%, 150 mL) and DCM (40 mL) mixture
  6. extractionthe aqueous layer was extracted by DCM (2×20 mL)
  7. washThe combined DCM layers were washed by water (2×20 mL)
  8. concentrationconcentrated
  9. customto afford white solid, which
  10. customwas purified via silica gel chromatography (40 g, 40% EtOAc:Heptane)

Sources & evidence

ORD record
ord-d9cc378d12d54f479c756224ba124185
Source dataset
uspto-grants-2010_11
Patent number
US07834039B2

Reaction notes

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