Job/Unit: O42782
/KAP1
Date: 04-09-14 18:37:37
Pages: 8
A. B. Khemnar, B. M. Bhanage
FULL PAPER
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[4-(tert-Butyl)phenyl][2-(1H-pyrazol-1-yl)phenyl]methanone
(3q):
Pale yellow solid (79%). 1H NMR (400 MHz, CDCl3): δ = 7.62–
7.60 (m, 5 H), 7.53–7.51 (m, 1 H), 7.47–7.43 (m, 2 H), 7.32 (t, J =
8 Hz, 2 H), 6.18 (t, J = 2 Hz, 1 H), 1.29 (s, 9 H) ppm. 13C NMR
(100 MHz, CDCl3): δ = 195.5, 156.8, 141.2, 138.6, 134.2, 134.1,
131.0, 129.8, 129.6, 129.3, 127.3, 125.5, 123.6, 107.5, 35.1,
31.0 ppm. HRMS (ESI, ion trap): calcd. for C20H21N2O [M +
H]+ 305.1654; found 305.1649. GC–MS (EI, 70 eV): m/z (%) = 304
(5.4) [M]+, 276 (28.3), 275 (100), 261 (19.1), 171 (29.6).
(4-Chlorophenyl)[2-(1H-pyrazol-1-yl)phenyl]methanone (3r): Pale
yellow solid (72%). 1H NMR (400 MHz, CDCl3): δ = 7.63–7.61
(m, 2 H), 7.58–7.53 (m, 4 H), 7.51–7.47 (m, 2 H), 7.26–7.21 (m, 2
H), 6.21 (t, J = 2 Hz, 1 H) ppm. 13C NMR (100 MHz, CDCl3): δ
= 194.6, 141.4, 139.2, 135.3, 133.4, 131.8, 130.3, 129.8, 129.4, 128.9,
128.5, 127.6, 123.1, 107.9 ppm. HRMS (ESI, ion trap): calcd. for
C16H12ClN2O [M + H]+ 283.0638; found 283.0630. GC–MS (EI,
70 eV): m/z (%) = 282 (5.8) [M]+, 255 (34.4), 254 (25.6), 253 (100),
171 (22.6), 139 (14.7), 111 (24.4), 75 (13).
[2]
(3-Chlorophenyl)[2-(1H-pyrazol-1-yl)phenyl]methanone (3s): Pale
yellow solid (70%). 1H NMR (400 MHz, CDCl3): δ = 7.66–7.62
(m, 2 H), 7.60–7.56 (m, 3 H), 7.53–7.45 (m, 2 H), 7.41–7.36 (m, 2
H), 7.20 (t, J = 8 Hz, 1 H), 7.61 (t, J = 2 Hz, 1 H) ppm. 13C NMR
(100 MHz, CDCl3): δ = 194.3, 141.3, 138.5, 134.4, 132.7, 131.6,
130.0, 129.4, 129.3, 129.0, 128.7, 127.6, 127.0, 125.7, 123.0,
108.0 ppm. HRMS (ESI, ion trap): calcd. for C16H12ClN2O [M +
H]+ 283.0638; found 283.0632. GC–MS (EI, 70 eV): m/z (%) = 282
(6.1) [M]+, 256 (10.5), 255 (34.4), 254 (32.7), 253 (100), 171 (33),
111 (21.9), 89 (10.8), 75 (12.6).
(2-Chlorophenyl)[2-(1H-pyrazol-1-yl)phenyl]methanone (3t): Pale
[3]
1
yellow solid (62%). H NMR (400 MHz, CDCl3): δ = 7.73 (dd, J
= 1.4, 7.6 Hz, 1 H), 7.64 (ddd, J = 1.5, 6.2, 7.6 Hz, 1 H), 7.57 (d,
J = 2.4 Hz, 1 H), 7.53–7.48 (m, 2 H), 7.41 (d, J = 1.6 Hz, 1 H),
7.29–7.20 (m, 3 H), 7.11–7.07 (m, 1 H), 6.13 (t, J = 2.16 Hz, 1 H)
ppm. 13C NMR (100 MHz, CDCl3): δ = 193.9, 141.3, 139.3, 136.7,
134.5, 132.7, 132.3, 132.0, 130.9, 130.8, 130.5, 129.8, 128.0, 126.0,
124.2, 107.6 ppm. HRMS (ESI, ion trap): calcd. for C16H12ClN2O
[M + H]+ 283.0638; found 283.0634. GC–MS (EI, 70 eV): m/z (%)
= 282 (1) [M]+, 253 (13), 248 (13.1), 247 (71.5), 220 (17.9), 219
(100), 171 (11.9), 139 (12.6), 111 (21.4), 89 (10.6), 75 (13.7).
[4]
[5]
(3-Bromophenyl)[2-(1H-pyrazol-1-yl)phenyl]methanone (3u): Pale
1
yellow solid (64%). H NMR (400 MHz, CDCl3): δ = 7.75 (t, J =
1.8 Hz, 1 H), 7.68–7.62 (m, 2 H), 7.59–7.45 (m, 5 H), 7.38 (d, J =
1.6 Hz, 1 H), 7.14 (t, J = 3.76 Hz, 1 H), 6.21 (t, J = 2.16 Hz, 1 H)
ppm. 13C NMR (100 MHz, CDCl3): δ = 194.2, 141.4, 138.6, 135.6,
131.7, 131.6, 130.3, 130.0, 129.7, 129.3, 127.7, 127.5, 126.2, 123.0,
122.4, 108.1 ppm. HRMS (ESI, ion trap): calcd. for C16H12BrN2O
[M + H]+ 327.0133; found 327.0129. GC–MS (EI, 70 eV): m/z (%)
= 326 (6.3) [M]+, 300 (32.6), 299 (97.5), 298 (34.2), 297 (100), 219
(13), 218 (16.7), 185 (10.7), 171 (52.3), 157 (16.7), 155 (17.6), 145
(13.7), 116 (16.), 89 (18.8), 77 (10.4), 76 (24.5), 75 (16.6), 50 (11.5).
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[10]
Supporting Information (see footnote on the first page of this arti-
1
cle): Temperature program for the GC–MS analysis, copies of H
[11]
[12]
and 13C NMR spectra.
Acknowledgments
[13]
[14]
A. B. K. is grateful to the Council of Scientific and Industrial Re-
search (CSIR), New Delhi, India for providing a senior research
fellowship (SRF).
A. Tlili, J. Schranck, J. Pospech, H. Neumann, M. Beller, An-
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