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Letter
Synlett
References and Notes
(21) N-(6-Nitropyridin-3-yl)benzamide (10); Typical Procedure:
To an oven-dried Radley’s reaction tube containing potassium
{phenyl[(trimethylsilyl)oxy]methylene}amide (2; 200 mg, 0.86
mmol, 1 equiv) was added 20 mol% Pd2(dba)3 (158.2 mg, 0.16
mmol, 0.2 equiv) and 20 mol% XPhos (82.3 mg, 0.16 mmol, 0.2
equiv). The reaction tube was then purged and 1,4-dioxane (8.6
mL) was added. The reaction mixture was then heated at 100 °C
for 10 min. 5-Bromo-2-nitropyridine (140 mg, 0.69 mmol, 0.8
equiv) was then added, the reaction tube was purged, and the
reaction mixture was then heated at 100 °C for 16 h. The reac-
tion mixture was taken up in EtOAc (30 mL) and washed with
brine (3 × 30 mL). The organics were extracted, dried, and con-
centrated to a residue, which was purified by flash column
chromatography [EtOAc–petroleum ether (40–60 °C), 30%] to
afford the title compound (135.4 mg, 81%) as an orange–brown
solid. IR (neat): 3319, 1683, 1612, 1519, 1495, 1346, 703,
770 cm–1; 1H NMR (500 MHz, DMSO-d6): δ = 11.02 (s, 1 H), 9.00
(d, J = 2.5 Hz, 1 H), 8.62 (dd, J = 8.9, 2.5 Hz, 1 H), 8.40 (d,
J = 8.9 Hz, 1 H), 8.02–8.01 (m, 2 H), 7.66 (t, J = 7.4 Hz, 1 H), 7.59
(t, J = 7.6 Hz, 2 H); 13C NMR (126 MHz, DMSO-d6): δ = 166.4,
151.3, 141.3, 139.6, 133.7, 132.5, 129.1, 128.6, 128.0, 119.3;
HRMS: m/z [M + H+] calcd for C12H10N3O3: 244.0717; found:
244.0714.
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© Georg Thieme Verlag Stuttgart · New York — Synlett 2016, 27, 88–92