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The Journal of Organic Chemistry
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1134 cmꢀ1; H NMR (200 MHz, CDCl3): δ = 7.39 (s, 5H),
7.21ꢀ7.17 (m, 1H), 7.08ꢀ7.02 (m, 2H), 6.71 (s, 1H), 5.99ꢀ5.79
(m, 1H), 5.27ꢀ5.19 (m, 2H), 2.99 (d, J = 6.9 Hz, 2H), 2.39 (s,
3H); 13C{1H}NMR (50 MHz, CDCl3): δ = 173.8, 169.9, 151.9,
136.0, 134.1, 130.7, 130.3, 129.5, 129.2, 127.0, 126.8, 124.7,
120.4, 110.8, 63.3, 40.3, 21.9; HRMS (ESI): calcd for
C19H17NNaO3 (M+Na)+: 330.1101; found: 330.1107.
(s, 1H), 2.01 (s, 3H), 1.33 (s, 9H); 13C{1H}NMR (50 MHz,
CDCl3): δ = 174.0, 169.9, 151.6, 147.6, 136.1, 129.3, 129.0,
127.0, 126.9, 121.3, 110.2, 63.4, 34.7, 31.5, 21.8; HRMS
(ESI): calcd for C20H21NNaO3 (M+Na)+: 346.1414; found:
346.1414.
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Nꢀ(5ꢀtertꢀButylꢀ2,3ꢀdihydroꢀ2ꢀoxoꢀ3ꢀphenylbenzofuranꢀ3ꢀ
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yl)benzamide (4cb): colorless solid; yield (289 mg, 75%); mp:
222ꢀ223 C; IR (neat): νmax 3361, 3064, 1805, 1656, 1478,
o
Nꢀ(2,3ꢀDihydroꢀ5ꢀisopropylꢀ2ꢀoxoꢀ3ꢀphenylbenzofuranꢀ3ꢀ
yl)acetamide (4ba): colorless solid; yield (266 mg, 86%); mp
1135, 1064 cmꢀ1; 1H NMR (500 MHz, CDCl3): δ = 7.80 (d, J =
7.5 Hz, 2H), 7.55ꢀ7.51 (m, 3H), 7.46ꢀ7.41 (m, 6H), 7.37 (d, J
= 2.0 Hz, 1H), 7.14 (d, J = 8.5 Hz, 1H), 7.08 (s, 1H), 1.32 (s,
9H); 13C{1H}NMR (125 MHz, CDCl3): δ = 173.9, 166.2,
151.9, 147.8, 136.4, 132.3, 132.3, 129.6, 129.4, 128.7, 127.3,
127.3, 127.1, 126.5, 121.3, 110.6, 63.8, 34.8, 31.6; HRMS
(ESI): calcd for C25H23NNaO3 (M+Na)+: 408.1570; found:
408.1569.
o
165ꢀ166 C; IR (neat): νmax 3257, 3027, 1810, 1654, 1487,
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1065 cmꢀ1; H NMR (500 MHz, CDCl3): δ = 7.42ꢀ7.24 (m,
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6H), 7.16ꢀ7.05 (m, 2H), 6.78 (s, 1H), 2.97ꢀ2.92 (m, 1H), 1.93
(s, 3H), 1.27 (d, J = 1.0 Hz, 3H), 1.26 (d, J = 1.0 Hz, 3H);
13C{1H}NMR (125 MHz, CDCl3): δ = 173.9, 169.5, 152.0,
145.2, 136.1, 129.4, 129.1, 128.0, 127.1, 126.9, 122.3, 110.7,
63.4, 33.8, 24.2, 24.1, 22.1; HRMS (ESI): calcd for
C19H19NNaO3 (M+Na)+: 332.1257; found: 332.1253.
Nꢀ(5ꢀtertꢀButylꢀ2,3ꢀdihydroꢀ2ꢀoxoꢀ3ꢀphenylbenzofuranꢀ3ꢀyl)ꢀ
2ꢀphenylacetamide (4cc): colorless solid; yield (280 mg,
70%); mp 186ꢀ188 oC; IR (neat): νmax 3179, 3030, 1817, 1682,
Nꢀ(2,3ꢀDihydroꢀ5ꢀisopropylꢀ2ꢀoxoꢀ3ꢀphenylbenzofuranꢀ3ꢀ
yl)benzamide (4bb): colorless solid; yield (290 mg, 78%); mp
o
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193ꢀ194 C; IR (neat): νmax 3359, 3064, 1807, 1657, 1482,
1153, 1061 cmꢀ1; H NMR (200 MHz, CDCl3): δ = 7.48ꢀ7.44
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1066 cmꢀ1; H NMR (500 MHz, CDCl3): δ = 7.97 (d, J = 6.5
(m, 1H), 7.29ꢀ7.39 (m, 10H), 7.19ꢀ7.11 (m, 2H), 6.38 (s, 1H),
3.65 (ABq, J = 15.8 Hz, 2H), 1.35 (s, 9H); 13C{1H}NMR (50
MHz, CDCl3): δ = 173.8, 170.4, 151.9, 147.7, 136.2, 134.2,
129.4, 129.2, 129.1, 129.0, 127.5, 127.2, 126.8, 126.5, 121.0,
110.4, 63.5, 42.7, 34.7, 31.5; HRMS (ESI): calcd for
C26H25NNaO3 (M+Na)+: 422.1727; found: 422.1725.
Hz, 2H), 7.68 (d, J = 2.0 Hz, 3H), 7.59ꢀ7.55 (m, 5H), 7.48ꢀ
7.43 (m, 3H), 7.31ꢀ7.29 (m, 1H), 3.14ꢀ3.10 (m, 1H), 1.45ꢀ1.44
(m, 6H); 13C{1H}NMR (125 MHz, CDCl3): δ = 173.8, 173.8,
166.3, 166.3, 152.1, 152.1, 145.3,136.3, 136.1, 132.2, 132.1,
129.5, 129.4, 129.2, 128.6, 128.5, 128.1, 128.1, 127.2, 127.2,
127.1, 127.0, 126.9, 122.4, 122.4, 110.7,63.7, 63.7, 33.8, 33.8,
24.2, 24.2, 24.0, 24.0; HRMS (ESI): calcd for C24H21NNaO3
(M+Na)+: 394.1414; found: 394.1416.
Nꢀ(5ꢀtertꢀButylꢀ2,3ꢀdihydroꢀ2ꢀoxoꢀ3ꢀphenylbenzofuranꢀ3ꢀyl)ꢀ
butꢀ3ꢀenamide (4cd): colorless solid; yield (280 mg, 80%); mp
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212ꢀ213 C; IR (neat): νmax 3253, 3026, 1813, 1650, 1364,
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Nꢀ(2,3ꢀDihydroꢀ5ꢀisopropylꢀ2ꢀoxoꢀ3ꢀphenylbenzofuranꢀ3ꢀyl)ꢀ
2ꢀphenylacetamide (4bc): colorless solid; yield (285 mg,
74%); mp 224ꢀ225 oC; IR (neat): νmax 3176, 3027, 1816, 1640,
1486, 1345, 1060 cmꢀ1; 1H NMR (500 MHz, CDCl3): δ = 7.36ꢀ
7.22 (m, 10H), 7.07, (d, J = 8.5 Hz, 1H), 7.00 (s,1H), 6.46 (s,
1H), 3.57 (ABq, J = 16.0 Hz, 2H), 2.95ꢀ2.90 (m, 1H), 1.24 (d,
J = 7.0 Hz, 6H); 13C{1H}NMR (125 MHz, CDCl3): δ = 173.7,
170.3, 152.2, 145.3, 136.2, 134.2, 129.4, 129.2, 129.1, 129.1,
128.2, 127.6, 126.9, 126.7, 122.0, 110.8, 63.5, 42.7, 33.8, 24.2,
24.1; HRMS (ESI): calcd for C25H23NNaO3 (M+Na)+:
408.1570; found: 408.1573.
1064 cmꢀ1; H NMR (500 MHz, CDCl3): δ = 7.43ꢀ7.38 (m,
6H), 7.30 (s, 1H), 7.08 (d, J = 8.5 Hz, 1H), 6.70 (s, 1H), 5.93ꢀ
5.85 (m, 1H), 5.25ꢀ5.21 (m, 2H), 3.00 (bs, 2H), 1.34 (s, 9H);
13C{1H}NMR (125 MHz, CDCl3): δ = 173.8, 169.8, 151.8,
147.7, 136.2, 130.4, 129.4, 129.2, 127.1, 126.9, 126.6, 121.2,
120.2, 110.4, 63.4, 40.3, 34.7, 31.5; HRMS (ESI): calcd for
C22H23NNaO3 (M+Na)+: 372.1570; found: 372.1572.
Nꢀ(5ꢀBromoꢀ2,3ꢀdihydroꢀ2ꢀoxoꢀ3ꢀphenylbenzofuranꢀ3ꢀyl)acetꢀ
amide (4da): colorless solid; yield (246 mg, 71%); mp 220ꢀ
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221 C; IR (neat): νmax 3252, 3026, 1815, 1654, 1465, 1063
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cmꢀ1; H NMR (200 MHz, CDCl3): δ = 7.52 (dd, J = 8.5 Hz,
Nꢀ(2,3ꢀDihydroꢀ5ꢀisopropylꢀ2ꢀoxoꢀ3ꢀphenylbenzofuranꢀ3ꢀyl)
butꢀ3ꢀenamide (4bd): colorless solid; yield (268 mg, 80%);
mp 163ꢀ164 oC; IR (neat): νmax 3257, 3026, 1813, 1651, 1487,
1064 cmꢀ1; 1H NMR (200 MHz, CDCl3): δ = 7.38 (s, 5H), 7.25
(dd, J = 8.3, 1.9 Hz, 1H), 7.14 (d, J = 1.9 Hz, 1H), 7.06 (d, J =
8.3 Hz, 1H), 6.81 (s, 1H), 5.97ꢀ5.77 (m, 1H), 5.25ꢀ5.15 (m,
2H), 3.05ꢀ2.85 (m, 3H), 1.26 (d, J = 7.0 Hz, 6H);
13C{1H}NMR (50 MHz, CDCl3): δ = 173.8, 169.9, 152.0,
145.3, 136.1, 130.4, 129.4, 129.2, 128.1, 126.9, 126.8, 122.2,
120.1, 110.7, 63.3, 40.2, 33.8, 24.2, 24.1; HRMS (ESI): calcd
for C21H21NNaO3 (M+Na)+: 358.1414; found: 358.1409.
2.1 1H), 7.43 – 7.41 (m, 6H), 7.06 (d, J = 8.5 Hz, 1H), 6.64 (s,
1H), 1.98 (s, 3H); 13C{1H}NMR (50 MHz, CD3CN): δ =
172.9, 169.9, 152.4, 134.8, 132.6, 130.5, 129.2, 128.8, 127.2,
126.6, 116.2, 112.3, 62.9, 20.6; HRMS (ESI): calcd for
C16H12BrNNaO3 (M+Na)+: 367.9893; found: 367.9892.
Nꢀ(5ꢀBromoꢀ2,3ꢀdihydroꢀ2ꢀoxoꢀ3ꢀphenylbenzofuranꢀ3ꢀyl)butꢀ
3ꢀenamide (4dd): colorless solid; yield (290 mg, 78%); mp
o
184ꢀ185 C; IR (neat): νmax 3261, 3068, 1813, 1652, 1464,
1062 cmꢀ1; 1H NMR (200 MHz, CDCl3): δ = 7.53 (dd, J = 8.5,
2.0 Hz, 1H), 7.41 (m, 6H), 7.07 (d, J = 8.5 Hz, 1H), 6.61 (s,
1H), 6.02ꢀ5.81 (m, 1H), 5.31ꢀ5.23 (m, 2H), 3.04 (d, J = 6.9
Hz, 2H); 13C{1H}NMR (50 MHz, CDCl3): δ = 172.7, 170.2,
152.9, 135.0, 133.2, 130.0, 129.8, 129.4, 127.3, 126.6, 120.6,
116.9, 112.9, 63.1, 40.1; HRMS (ESI): calcd for
C18H14BrNNaO3 (M+Na)+: 394.0049; found: 394.0049.
Nꢀ(5ꢀtertꢀButylꢀ2,3ꢀdihydroꢀ2ꢀoxoꢀ3ꢀphenylbenzofuranꢀ3ꢀ
yl)acetamide (4ca): colorless solid; yield (262 mg, 81%); mp
o
156ꢀ157 C; IR (neat): νmax 3255, 3027, 1812, 1655, 1490,
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1064 cmꢀ1; H NMR (200 MHz, CDCl3): δ = 7.45ꢀ7.35 (m,
6H), 7.31 (d, J = 1.84 Hz, 1H), 7.08 (d, J = 8.5 Hz, 1H), 6.51
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