Chemical Papers
2‑(Chlorodifuoromethyl)‑1‑(2‑ethylphenyl)‑1H‑imida‑
zole‑5‑carbaldehyde (2m)
2‑(Difuoromethyl)‑1‑(4‑methoxyphenyl)‑1H‑imida‑
zole‑5‑carbaldehyde (2q)
1
White solid, m. p.: 77–78 ℃. 1H NMR (400 MHz, CDCl3)
δ 9.49 (s, 1H), 7.88 (s, 1H), 7.47 (m, 1H), 7.39 (m,
1H), 7.28 (m, 1H), 7.19 (m, 1H), 2.19 (m, 2H), 1.06 (t,
J = 8.0 MHz, 3H). 19F NMR (282 MHz, CDCl3) δ -48.87
(d, J=16.9 MHz, 2F). 13C NMR (101 MHz, CDCl3) δ 178.9,
144.0 (t, J=32.3 MHz), 141.1, 137.7, 134.5, 132.5, 130.9,
127.6, 126.7, 119.9 (t, J=299.0 MHz), 23.2, 13.5. MS (EI),
m/e (%): 284 (M+). HRMS (EI), Calcd. for C13H11ClF2N2O:
284.0528; Found: 284.0524.
White Solid, m. p.: 139–142 ℃. H NMR (400 MHz,
CDCl3) δ 9.57, 7.83, 7.22 (d, J=12.0 MHz, 2H), 6.94 (d,
J=12.0 MHz, 2H), 6.51 (t, J=52.0 MHz, 1H), 3.81 (s, 3H).
19F NMR (282 MHz, CDCl3) δ -113.86 (d, J=52.64 MHz).
13C NMR (101 MHz, CDCl3) δ 179.0, 160.7, 144.9 (t,
J=21.0 MHz), 138.5, 134.3, 128.4, 126.0, 114.6, 108.4 (t,
J=238.0 MHz), 55.6. MS (EI), m/e (%): 252 (M+). HRMS
(EI), Calcd. for C12H10F2N2O2: 252.0710; Found: 252.0709.
2‑(Difuoromethyl)‑1‑(naphthalen‑1‑yl)‑1H‑imida‑
zole‑5‑carbaldehyde (2r)
1‑(2‑Bromophenyl)‑2‑(chlorodifuoromethyl)‑1H‑imida‑
zole‑5‑carbaldehyde (2n)
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White solid, m. p.: 185–188 ℃. H NMR (400 MHz,
1
Light yellow solid. m. p.: 63–64 ℃. H NMR (400 MHz,
CDCl3) δ 9.43 (s, 1H), 7.98 (m, 2H), 7.90 (m, 1H), 7.49
(m, 4H), 7.03 (m, 1H), 6.41 (t, J = 12.0 MHz, 1H). 19F
NMR (282 MHz, CDCl3) δ -114.81 (qd, J1 = 39.5 MHz,
J2 =67.7 MHz). 13C NMR (101 MHz, CDCl3) δ 177.6, 144.4
(q, J=27.3 MHz), 137.3, 133.8, 132.9, 130.0, 129.0, 127.5,
127.3, 126.3, 124.8, 124.0, 120.1, 107.1 (t, J=239.4 MHz).
MS (EI), m/e (%): 272 (M+). HRMS (EI), Calcd. for
C15H10F2N2O: 272.0761; Found: 272.0759.
CDCl3) δ 9.61 (s, 1H), 7.86 (s, 1H), 7.67 (m, 1H), 7.40 (m,
3H). 19F NMR (282 MHz, CDCl3) δ -49.18 (q). 13C NMR
(101 MHz, CDCl3) δ 178.5, 143.8 (t, J=32.3 MHz), 138.5,
133.9, 133.8, 133.5, 131.9, 129.2, 128.3, 122.3, 119.7 (t,
J=289.9 MHz). MS (EI), m/e (%): 334 (M+). HRMS (EI),
Calcd. for C11H6ClBrF2N2O: 298.9632 (M-Cl); Found:
298.9628 (M-Cl).
2‑(Bromodifuoromethyl)‑1‑p‑tolyl‑1H‑imidazole‑5‑car‑
baldehyde (2o)
1‑(4‑Methoxyphenyl)‑2‑(perfuoroethyl)‑1H‑imida‑
zole‑5‑carbaldehyde (2s)
White solid (decompose in heating). 1H NMR (300 MHz,
CDCl3): δ 9.57 (s, 1H), 7.90 (s, 1H), 7.35 (d, J=8.4 MHz,
2H), 7.27 (d, J = 8.4 MHz, 2H), 2.47 (s, 3H). 19F NMR
(282 MHz, CDCl3): δ −44.97 (s). 13C NMR (101 MHz,
CDCl3): δ 188.0, 144.9 (t, J = 29.1 MHz), 140.8, 137.3,
134.7, 131.2, 130.0, 127.2, 111.2 (t, J = 300.4 MHz),
21.3. MS (EI), m/e (%): 314 (M+). HRMS (EI), Calcd. for
C12H9N2OF2Br: 313.9866; Found: 313.9861.
White solid, m. p.: 74–75 ℃. 1H NMR (400 MHz, CDCl3)
δ 9.52 (s, 1H), 7.87 (s, 1H), 7.20 (d, J = 12.0 MHz,
2H), 6.94 (d, J = 8.0 MHz, 2H), 3.81 (s, 3H). 19F NMR
(282 MHz, CDCl3) δ -82.30 (t, J=5.6 MHz, 3F), -108.29
(s, 2F). 13C NMR (101 MHz, CDCl3) δ 179.0, 160.9,
139.6 (t, J=54.5 MHz), 137.5, 135.2, 128.4, 126.1, 118.1
(qt, J1 = 287.9 MHz, J2 = 70.7 MHz), 114.5, 109.1 (tq,
J1 = 255.5 MHz, J2 = 39.4 MHz), 55.6. MS (EI), m/e (%):
272 (M+). HRMS (EI), Calcd. for C13H9F5N2O2: 320.0584;
Found: 320.0586. Anal. Calcd. for C13H9F5N2O2: C,48.76;
H, 2.83; N, 8.75; Found: C, 48.89; H, 2.89; N, 8.87.
2‑(Bromodifuoromethyl)‑1‑(2‑(trifuoromethyl)
phenyl)‑1H‑imidazole‑5‑carbaldehyde (2p)
White solid, m. p.: 69–71 ℃. 1H NMR (300 MHz, CDCl3): δ
9.71 (s, 1H), 7.96 (s, 1H), 7.87 (m, 1H), 7.75 (m, 2H), 7.51
(m, 1H). 19F NMR (282 MHz, CDCl3): δ -45.53 (s, 2F),
-60.70 (s, 3F). 13C NMR (101 MHz, CDCl3): δ 178.3, 145.6
(t, J=29.2 MHz), 139.2, 134.7, 132.9, 132.4, 130.9, 129.3,
127.6 (q, J=5.1 MHz), 122.8 (q, J=272.0 MHz), 110.7 (t,
J=301.1 MHz). MS (EI), m/e (%): 368 (M+). Anal. Calcd.
for C12H6BrF6N2O: C, 39.05; H, 1.66; N, 7.59; Found: C,
39.20; H, 1.66; N, 7.46.
5‑Iodo‑1‑(4‑methoxyphenyl)‑6‑phe‑
nyl‑2‑(trifuoromethyl)‑1,4‑dihydropyrimidine (2t)
Light yellow solid (decompose at rt). 1H NMR (300 MHz,
CDCl3): δ 7.18 (m, 3H), 7.00 (m, 2H), 6.91 (d, J=8.7 MHz,
2H), 6.61 (d, J=8.7 MHz), 4.85 (s, 2H), 3.69 (s, 3H). 19
F
NMR (282 MHz, CDCl3): δ -65.53 (s). 13C NMR (101 MHz,
CDCl3): δ 159.2, 145.5 (q, J = 33.5 MHz), 143.3, 136.6,
131.7, 131.1, 130.0, 128.6, 128.1, 117.7 (q, J=277.1 MHz),
113.7, 73.6, 57.6, 55.3. MS (ESI): 459.3 (M+H+). HRMS
(ESI), Calcd. for C18H15F3IN2O: 459.0181; Found:
459.0187.
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