5-(2-Pyridyl)oxazole → 1-Oxo-1-[5-(2-pyridyl)oxazol-2-yl]-3-(4-(phenylthio)phenyl)propane

HRID 386442Notes

Reaction equation

HRID 386442 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[O:11][CH:10]=[N:9][CH:8]=1.[C:12]1([S:18][C:19]2[CH:24]=[CH:23][C:22]([CH2:25][CH2:26][C:27](O)=[O:28])=[CH:21][CH:20]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>>[O:28]=[C:27]([C:10]1[O:11][C:7]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=2)=[CH:8][N:9]=1)[CH2:26][CH2:25][C:22]1[CH:23]=[CH:24][C:19]([S:18][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:20][CH:21]=1

Participants

3

Reactant 2

HCID 7371945-(2-Pyridyl)oxazoleHCID 67125535HCID 67125535, compound

Product 1

HCID 167360091-Oxo-1-[5-(2-pyridyl)oxazol-2-yl]-3-(4-(phenylthio)phenyl)propaneYield 33%

Procedure

The title compound was prepared from 5-(2-pyridyl)oxazole and 3-(4-(phenylthio)phenyl)propanoic acid (S44) using General Procedure B. PTLC (SiO2, 50% EtOAc-hexanes) afforded 11i (50 mg, 0.13 mmol, 33%) as an orange solid: 1H NMR (CDCl3, 500 MHz) 8.68-8.66 (m, 1H), 7.88 (s, 1H), 7.88-7.85 (m, 1H), 7.82 (td, 1H, J=7.7, 1.8 Hz), 7.34-7.28 (m, 7H), 7.24-7.20 (m, 2H), 3.46 (t, 2H, J=7.4 Hz), 3.10 (t, 2H, J=7.4 Hz); 13C NMR (CDCl3, 125 MHz) 187.1, 157.1, 153.4, 150.1, 146.2, 139.7, 137.1, 136.3, 132.9, 131.8, 130.4, 129.4, 129.1, 126.9, 126.7, 124.2, 120.4, 40.4, 29.2; IR (film) νmax 3054, 2925, 2855, 1698, 1601, 1581, 1505, 1470, 1427, 1381, 1282, 1083, 990, 963, 913, 818, 784, 740, 691 cm−1; ESI-TOF m/z 387.1170 (C23H18N2O2S+H+ requires 387.1162).

Sources & evidence

ORD record
ord-36e1f28df5a4460dac5e6070391df965
Source dataset
uspto-grants-2013_02
Patent number
US08372823B2

Reaction notes

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