5-(2-Pyridyl)oxazole → HCID 16736226, compound

HRID 386431Notes

Reaction equation

HRID 386431 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.[O:12]([CH2:19][C:20]1[CH:25]=[CH:24][C:23]([CH2:26][CH2:27][C:28](O)=[O:29])=[CH:22][CH:21]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>>[O:12]([CH2:19][C:20]1[CH:21]=[CH:22][C:23]([CH2:26][CH2:27][C:28]([C:10]2[O:11][C:7]([C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=3)=[CH:8][N:9]=2)=[O:29])=[CH:24][CH:25]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

3

Reactant 2

HCID 7371945-(2-Pyridyl)oxazoleHCID 545821483-[4-(Phenoxymethyl)phenyl]propanoic acid

Product 1

HCID 16736226HCID 16736226, compoundYield 32%

Procedure

The title compound (11e) was prepared from 5-(2-pyridyl)oxazole and 3-(4-(phenoxymethyl)phenyl)propanoic acid (S27) using General Procedure B. PTLC (SiO2, 50% EtOAc-hexanes) afforded 11e (40 mg, 0.10 mmol, 32%) as a pale yellow solid: 1H NMR (CDCl3, 400 MHz) 8.68-8.66 (m, 1H), 7.89 (s, 1H), 7.88-7.85 (m, 1H), 7.81 (td, 1H, J=7.9, 1.5 Hz), 7.38 (d, 2H, J=8.2 Hz), 7.34-7.27 (m, 5H), 6.99-6.94 (m, 3H), 5.03 (s, 2H), 3.48 (t, 2H, J=7.4 Hz), 3.13 (t, 2H, J=7.5 Hz); 13C NMR (CDCl3, 100 MHz) 187.2, 158.7, 157.1, 153.3, 150.1, 146.2, 140.1, 137.1, 137.0, 129.4, 128.6, 127.8, 126.9, 124.1, 120.8, 120.3, 114.7, 69.6, 40.5, 29.3; IR (film) νmax 2923, 1694, 1601, 1504, 1470, 1428, 1380, 1241, 1171, 1125, 1080, 1032, 1017, 989, 962, 911, 869, 815, 788, 760, 693 cm−1; ESI-TOF m/z 385.1550 (C24H20N2O3+H+ requires 385.1547).

Sources & evidence

ORD record
ord-c49c63b5d38f4a81be31f4c14643e585
Source dataset
uspto-grants-2013_02
Patent number
US08372823B2

Reaction notes

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