6-Methoxy-5-(4-Methyl-1H-Imidazol-1-Yl)Picolinonitrile synthesis
- Product Name:6-Methoxy-5-(4-Methyl-1H-Imidazol-1-Yl)Picolinonitrile
- CAS Number:1241428-31-8
- Molecular formula:C11H10N4O
- Molecular Weight:214.22
557-21-1
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Yield: 88%
Reaction Conditions:
with (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride;tris-(dibenzylideneacetone)dipalladium(0) in N,N-dimethyl-formamide at 20 - 140; for 2 h;
Steps:
184 6-methoxy-5-(4-methyl-]H-imidazol-] -yl) picolinonitrile:
To a stirred solution6-bromo-2-methoxy-3-(4-methyl-1H-imidazol-1-yl) pyridine (20 g, 74 mmol) in DMF (240 mL) at room temperature under an argon atmosphere were added Pd(dppf)2C12 (500 mg, 0.9 mmol), Pd2(dba)3 (682 mg, 0.7 mmol) and zinc cyanide (5.3 g, 45 mmol). The reaction mixture was stirred at 140 °C for 2 h. After consumption of starting material (monitored by TLC), the reaction mixture was diluted with 25% NH4OH solution (240 mL) to afford the solid. The solid was collected by filtration and dried in vacuo to afford 6-methoxy-5-(4- methyl-1H-imidazol-1-yl) picolinonitrile (14 g, 88%) as a pale yellow solid.[0872] ‘H NMR (CDC13: 400 MHz): 7.89 (s, 1H), 7.63 (d, 1H), 7.43 (d, 1H), 7.01 (s, 1H), 4.09 (s, 3H), 2.30 (s, 3H); LCMS: 98.7%; 214.9 (M+1); (column; Ascentis Express C-18 (50 x 3.0 mm, 2.7 pm); RT 1.19 mm; mobile phase: 0.025% Aq TFA+5% ACN:ACN+5% 0.025% Aq TFA; T/B%: 0.0 1/5, 0.5/5, 3/100, 5/100; flow rate: 1.2 mL/min) (Gradient); TLC: EtOAc (R1 0.3).
References:
FORUM PHARMCEUTICALS INC.;ACHARYA, Raksha;BURNETT, Duane, A.;BURSAVICH, Matthew, Gregory;COOK, Andrew, Simon;HARRISON, Bryce, Alden;MCRINER, Andrew, J. WO2016/201168, 2016, A1 Location in patent:Paragraph 0871; 0872
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