2-Nitroimidazole → HCID 86724819, compound

HRID 1525584Notes

Reaction equation

HRID 1525584 reaction equation
Br[CH2:2][CH2:3][O:4][C:5]1[CH:6]=[C:7]([CH2:13][C@@H:14]([CH3:28])[C@@H:15]([CH3:27])[CH2:16][C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[C:19]([O:25][CH3:26])[CH:18]=2)[CH:8]=[CH:9][C:10]=1[O:11][CH3:12].C[O-].[Na+].[N+:32]([C:35]1[NH:36][CH:37]=[CH:38][N:39]=1)([O-:34])=[O:33]>>[CH3:26][O:25][C:19]1[CH:18]=[C:17]([CH2:16][C@H:15]([CH3:27])[C@H:14]([CH3:28])[CH2:13][C:7]2[CH:8]=[CH:9][C:10]([O:11][CH3:12])=[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])[CH:6]=2)[CH:22]=[CH:21][C:20]=1[O:23][CH3:24]

Participants

4

Reactant 3

HCID 107012-NitroimidazoleHCID 10942334Sodium MethoxideHCID 86724818HCID 86724818, compound

Product 1

HCID 86724819HCID 86724819, compoundYield 53%

Procedure

The Standard Procedure 2 was followed by use of 5a (57.9 mg, 0.129 mmol, 1.0 equiv), sodium methoxide (15.4 mg, 0.285 mmol, 2.2 equiv), and 2-nitroimidazole (6b, 29.3 mg, 0.259 mmol, 2.0 equiv). After workup and purification with column chromatography (80% EtOAc in hexanes as eluant), 7b (32.9 mg, 0.0682 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), 0.82 (d, J=6.8 Hz, 3H, CH3), 1.70-1.72 (m, 2H, 2×CH), 2.21-2.31 (m, 2H, 2×ArCH), 2.67-2.73 (m, 2H, 2×ArCH), 3.75 (s, 3H, OCH3), 3.83 (s, 3H, OCH3), 3.85 (s, 3H, OCH3), 4.30 (t, J=3.8 Hz, 2H, CH2N), 4.81 (t, J=4.6 Hz, 2H, CH2O), 6.56 (m, 1H, ArH), 6.63-6.68 (m, 2H, 2×ArH), 6.71-6.78 (m, 2H, 3×ArH), 7.13 (s, 1H, nitroimidazole C5-H), 7.35 (s, 1H, nitroimidazole C4-H); 13C NMR (CDCl3, 100 MHz) δ 15.95, 15.99, 38.27, 38.68, 38.94, 39.02, 49.41, 55.59, 55.62, 55.69, 67.78, 110.86, 111.68, 112.12, 115.69, 120.73, 122.78, 127.46, 127.87, 134.18, 134.46, 144.51, 146.72, 146.82, 147.68, 148.43; IR (neat) 2924 (s), 2851 (s), 1588 (w), 1537 (w), 1515 (s), 1488 (w), 1361 (s), 1260 (s), 1235 (s), 1028 (s) cm−1; HRMS (FAB) m/z calcd for C26H34N3O6 (M+H)+: 484.2448. found: 484.2433.

Workup

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

Sources & evidence

ORD record
ord-5af48b4724f04f1cb4df0a0a426f8a58
Source dataset
uspto-grants-2015_07
Patent number
US09084779B2

Reaction notes

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