2-Bromobenzonitrile → HCID 19008910, compound

HRID 1742432Notes

Reaction equation

HRID 1742432 reaction equation
[CH2:1]([C:5]1[N:13]([C:14]2[C:23]3[C:18](=[CH:19][C:20]([Sn](CCCC)(CCCC)CCCC)=[CH:21][CH:22]=3)[CH:17]=[CH:16][CH:15]=2)[C:8]2=[N:9][CH:10]=[CH:11][CH:12]=[C:7]2[N:6]=1)[CH2:2][CH2:3][CH3:4].Br[C:38]1[CH:45]=[CH:44]C=C[C:39]=1[C:40]#[N:41].O1[CH2:51][CH2:50]OCC1>>[CH2:1]([C:5]1[N:13]([C:14]2[CH:15]=[CH:16][CH:17]=[C:18]3[C:23]=2[CH:22]=[CH:21][C:20]([C:51]2[CH:50]=[CH:44][CH:45]=[CH:38][C:39]=2[C:40]#[N:41])=[CH:19]3)[C:8]2=[N:9][CH:10]=[CH:11][CH:12]=[C:7]2[N:6]=1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 3

HCID 162722-BromobenzonitrileHCID 312751,4-DioxaneHCID 19008942HCID 19008942, compound

Product 1

HCID 19008910HCID 19008910, compound

Conditions

Temperature
23 °C

Procedure

To a solution of 2-butyl-3-(6-tributylstannanyl-naphthalen-1-yl)-3H-imidazo[4,5-b]pyridine (310 mg, 0.56 mmol) in anhydrous dioxane (1.5 mL) was added 2-bromobenzonitrile (109 mg, 0.6 mmol) and PdCl2 (PPh3)3 (44 mg, 0.06 mmol). The reaction mixture was heated under reflux for 17 hours, cooled to 23° C. and concentrated in vacuo. The crude residue was chromatographed on SiO2 -gel using 30% ethyl acetate/hexanes to give 85 mg of the desired product. 1H NMR (250 MHz, CDCl3): d 8.28 (d, 1 H), 8.25 (s, 1 H), 8.17 (dd, 2 H), 7.60 (m, 7 H), 7.28 (m, 2.70 (t, 2 H), 1.76 (m, 2 H), 1.32 (m, 2 H), 0.83 (t, 3 H).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 17 hours
  3. concentrationconcentrated in vacuo
  4. customThe crude residue was chromatographed on SiO2

Sources & evidence

ORD record
ord-54a9cbd3de7a49b097f9a620b1419d82
Source dataset
uspto-grants-1994_08
Patent number
US05338740

Reaction notes

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