تفاعل #44549

معادلة التفاعل

potassium tert-butoxide

2-(3-acetamidophenyl)-6-chloropyrazine

tert-butyl 2-(3-aminophenoxy)ethylcarbamate

1,3-bis(2,6-di-i-propylphenyl)-4,5-dihydro-imidazolium tetra-fluoroborate

→

title compound

المردود 43.0%

tert-butyl 2-(3-(6-(3-acetamidophenyl)pyrazin-2-ylamino)phenoxy)ethylcarbamate

المردود 43.0%

المذيبات

dioxane

ظروف التفاعل

المعالجة

1. 1
   أخرىwere reacted at 100° C. for 20 minutes with microwave heating
2. 2
   ترشيحThe reaction mixture was filtered
3. 3
   غسيلwashed with ethyl acetate (45 mL)
4. 4
   أخرىThe resulting liquid was dried under vacuo
5. 5
   أخرىto give a paste that
6. 6
   أخرىwas chromatographed
7. 7
   workup.ADDITIONa mixture of ethyl acetate:dichloromethane (1:1) as eluent

الإجراء التجريبي

Using Method O, 2-(3-acetamidophenyl)-6-chloropyrazine (150 mg, 0.61 mmol), tert-butyl 2-(3-aminophenoxy)ethylcarbamate (CJS 700, 190 mg, 0.753 mmol), tris(dibenzylideneacetone) dipalladium (0) (28 mg, 0.030 mmol), 1,3-bis(2,6-di-i-propylphenyl)-4,5-dihydro-imidazolium tetra-fluoroborate (29 mg, 0.061 mmol) and potassium tert-butoxide (102 mg, 0.91 mmol), and dioxane (3.5 mL) were reacted at 100° C. for 20 minutes with microwave heating. The reaction mixture was filtered and washed with ethyl acetate (45 mL). The resulting liquid was dried under vacuo to give a paste that was chromatographed using a mixture of ethyl acetate:dichloromethane (1:1) as eluent to furnish 120 mg of the title compound. Yield: 43%. 1H NMR (250 MHz, DMSO-d6) δ 1.37 (s, 9 H), 2.09 (s, 3 H), 3.32 (m, 2 H), 3.98 (m, 2 H), 6.56 (dd, 1 H, Ja=8.0 Hz, Jb=2.4 Hz), 7.01 (bt, 1 H), 7.25 (t, 1 H, J=8.1 Hz), 7.36 (bd, 1 H, J=8.4 Hz), 7.45 (t, 1 H, J=7.9 Hz), 7.59 (bs, 1 H), 7.66 (bd, 1 H, J=9.2 Hz), 7.74 (bd, 1 H, J=8.0 Hz), 8.19 (s, 1 H), 8.34 (bs, 1 H), 8.42 (s, 1 H), 9.60 (s, 1 H), 10.09 (s, 1 H). 13C NMR (62.5 MHz, DMSO-d6) δ 23.99, 28.18, 66.23, 77.77, 103.95, 107.82, 110.74, 117.11, 120.07, 121.24, 129.24, 129.66, 130.08, 133.66, 137.10, 139.90, 141.88, 147.96, 151.44, 155.65, 158.87, 168.53. m/z 364.2 [(M-Boc+H)+ calc for C20H21N5O2 363.2].

المصدر