2-Nitroimidazole → HCID 71076599, compound

HRID 1525588Notes

Reaction equation

HRID 1525588 reaction equation
Br[CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C@@H:12]([CH3:26])[C@@H:13]([CH3:25])[CH2:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[C:17]([O:23][CH3:24])[CH:16]=2)=[CH:7][C:6]=1[O:27][CH3:28].C[O-].[Na+].[N+:32]([C:35]1[NH:36][CH:37]=[CH:38][N:39]=1)([O-:34])=[O:33]>>[CH3:24][O:23][C:17]1[CH:16]=[C:15]([CH2:14][C@H:13]([CH3:25])[C@H:12]([CH3:26])[CH2:11][C:8]2[CH:9]=[CH:10][C:5]([O:4][CH2:3][CH2:2][N:36]3[CH:37]=[CH:38][N:39]=[C:35]3[N+:32]([O-:34])=[O:33])=[C:6]([O:27][CH3:28])[CH:7]=2)[CH:20]=[CH:19][C:18]=1[O:21][CH3:22]

Participants

4

Reactant 3

HCID 107012-NitroimidazoleHCID 10942334Sodium MethoxideHCID 86724824HCID 86724824, compound

Product 1

HCID 71076599HCID 71076599, compoundYield 53%

Procedure

The Standard Procedure 2 was followed by use of 9a (38.2 mg, 0.0849 mmol, 1.0 equiv), sodium methoxide (10.1 mg, 0.187 mmol, 2.2 equiv), and 2-nitroimidazole (6b, 19.2 mg, 0.170 mmol, 2.0 equiv). After workup and purification with column chromatography (80% EtOAc in hexanes as eluant), 10b (21.6 mg, 0.0447 mmol) was obtained in 53% yield as a yellow gummy oil: 1H NMR (CDCl3, 400 MHz) δ 0.79 (d, J=6.8 Hz, 3H, CH3), 0.81 (d, J=6.8 Hz, 3H, CH3), 1.72-1.73 (m, 2H, 2×CH), 2.23-2.32 (m, 2H, 2×ArCH), 2.68-2.74 (m, 2H, 2×ArCH), 3.73 (s, 3H, OCH3), 3.82 (s, 3H, OCH3), 3.83 (s, 3H, OCH3), 4.30 (t, J=4.6 Hz, 2H, CH2N), 4.80 (t, J=4.8 Hz, 2H, CH2O), 6.59-6.70 (m, 5H, 5×ArH), 6.75-6.77 (m, 1H, ArH), 7.13 (s, 1H, nitroimidazole C5-H), 7.34 (s, 1H, nitroimidazole C4-H); 13C NMR (CDCl3, 100 MHz) δ 16.04, 16.16, 38.69, 38.88, 39.05, 39.21, 49.64, 55.59, 55.72, 55.81, 68.30, 110.92, 112.16, 112.87, 115.24, 120.84, 121.02, 127.51, 128.03, 134.26, 136.84, 144.64, 145.10, 146.97, 148.60, 149.68; IR (neat) 2924 (s), 2853 (s), 1590 (w), 1539 (m), 1516 (s), 1456 (w), 1361 (s), 1261 (s), 1235 (s), 1030 (s) cm−1; HRMS (FAB) m/z calcd for C26H34N3O6 (M+H)+: 484.2448. found: 484.2457.

Workup

  1. customAfter workup and purification with column chromatography (80% EtOAc in hexanes as eluant)

Sources & evidence

ORD record
ord-acbd8b90367f4c8f9c3cd91ca923a42f
Source dataset
uspto-grants-2015_07
Patent number
US09084779B2

Reaction notes

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