Orm-10103 → 2-(4-Chlorophenyl)-6-(5-nitropyridin-2-yloxy)chroman-4-ol

HRID 31277Notes

Reaction equation

HRID 31277 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7](OC2C=C3C(=CC=2)OC(C2C=CC=CC=2)CC3)=[N:8][CH:9]=1)([O-:3])=[O:2].[Cl:27][C:28]1[CH:33]=[CH:32][C:31]([CH:34]2[CH2:43][CH:42]([OH:44])[C:41]3[C:36](=[CH:37][CH:38]=[C:39]([OH:45])[CH:40]=3)[O:35]2)=[CH:30][CH:29]=1>>[Cl:27][C:28]1[CH:33]=[CH:32][C:31]([CH:34]2[CH2:43][CH:42]([OH:44])[C:41]3[C:36](=[CH:37][CH:38]=[C:39]([O:45][C:7]4[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][N:8]=4)[CH:40]=3)[O:35]2)=[CH:30][CH:29]=1

Participants

3

Reactant 2

HCID 17978512Orm-10103HCID 179786362-(4-Chlorophenyl)chroman-4,6-diol

Product 1

HCID 179785922-(4-Chlorophenyl)-6-(5-nitropyridin-2-yloxy)chroman-4-ol

Procedure

2-(4-Chlorophenyl)-6-(5-nitropyridin-2-yloxy)chroman-4-ol was prepared as described for 5-nitro-2-(2-phenylchroman-6-yloxy)pyridine in Example 1(b) starting from 330 mg of 2-(4-chlorophenyl)chroman-4,6-diol. The product was purified by column chromatography using heptane-ethyl acetate (2:1) as an eluant. 1H NMR (300 MHz, d6-DMSO) δ: 9.04 (d, 1H, J 2.9 Hz), 8.61 (dd, 1H, J 9.1, 2.9 Hz), 7.54-7.47 (m, 4H), 7.25 (d, 1H, J 2.8 Hz), 7.22 (d, 1H, 9.1 Hz), 7.02 (dd, 1H, J 8.8, 2.8 Hz), 6.89 (d, 1H, J 8.8 Hz), 5.65 (d, 1H, J 6.4 Hz), 5.33 (d, 1H, J 10.6 Hz), 4.98 (m, 1H), 2.34 (m, 1H), 1.94 (m, 1H).

Workup

  1. customThe product was purified by column chromatography

Sources & evidence

ORD record
ord-3b07c4efa6d34dfa9982f0ebc5ab37a5
Source dataset
uspto-grants-2008_09
Patent number
US07425568B2

Reaction notes

Loading…