Orm-10103 → 2-[2-(2,4-Dichlorophenyl)chroman-6-yloxy]-5-nitropyridine

HRID 31182Notes

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

Participants

Reactant 2

HCID 17978512Orm-10103

HCID 179785552-(2,4-Dichlorophenyl)chroman-6-ol

Product 1

HCID 179786262-[2-(2,4-Dichlorophenyl)chroman-6-yloxy]-5-nitropyridine

Procedure

2-[2-(2,4-dichlorophenyl)chroman-6-yloxy]-5-nitropyridine was prepared as described for 5-nitro-2-(2-phenylchroman-6-yloxy)pyridine in Example 1(b) starting from 530 mg of 2-(2,4-dichlorophenyl)chroman-6-ol. The product was purified on preparative TLC-plate covered with silica gel using heptane-ethyl acetate (3:1) as an eluant. 1H NMR (400 MHz, CDCl3) δ: 9.06 (d, 1H, J 2.7 Hz), 8.47 (dd, 1H, J 9.0, 2.7 Hz), 7.56 (d, 1H, J 8.4 Hz), 7.41 (d, 1H, J 2.0 Hz), 7.33 (dd, 1H, J 8.4, 2.0 Hz) 7.02 (d, 1H, J 9.0 Hz), 6.99-6.92 (m, 3H), 5.39 (dd, 1H, J 10.4, 2.2 Hz), 3.06 (ddd, 1H, J −16.9, 11.9, 6.0 Hz), 2.83 (ddd, 1H, J −16.9, 5.3, 2.7 Hz), 2.34 (m, 1H), 1.89 (m, 1H).

Workup

customThe product was purified on preparative

Sources & evidence

ORD record: ord-6d803267e10d4763bbbd1261283274d3
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07425568B2

Reaction notes

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