Dimethylformamide → 5-{[(Propan-2-yl)oxy]methyl}pyridine-2-carbonitrile

HRID 1958391Notes

Reaction equation

Cl[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][O:9][CH:10]([CH3:12])[CH3:11])=[CH:4][N:3]=1.[CH3:13][N:14](C=O)C>[C-]#N.[C-]#N.[Zn+2].C(Cl)Cl.O>[CH:10]([O:9][CH2:8][C:5]1[CH:6]=[CH:7][C:2]([C:13]#[N:14])=[N:3][CH:4]=1)([CH3:12])[CH3:11]

Participants

Conditions

Temperature: 180 °C

Procedure

In a microwave reaction tube was placed 2-chloro-5-isopropoxymethyl-pyridine (0.12 g, 0.66 mmol), Zn(CN)2 (0.077 g, 0.66 mmol), tetrakis(triphenylphosphino)dipalladium (76 mg, 0.066 mmol), DMF (2 mL). The reaction mixture was heated at 180° C. for 5 minutes. The resulted mixture was worked up by CH2Cl2/H2O. The CH2Cl2 layer was dried and concentrated to give the crude product. The crude was purified by column chromatography by using 30% EtOAc/Hexane. 1H NMR (CDCl3, 400 MHz) δ 1.26 (d, 6H), 3.73 (m, 1H), 4.59 (s, 2H), 7.68 (d, 1H), 7.85 (m, 1H), 8.67 (s, 1H). Exact mass calculated for C10H12N2O 176.09, found 177.2 (MH+).

Workup

customIn a microwave reaction tube
dry with materialThe CH2Cl2 layer was dried
concentrationconcentrated

Sources & evidence

ORD record: ord-42854645e59f4994a7fff712a0820b1a
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08410119B2

Reaction notes

Loading…