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

HRID 31264Notes

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].[F:27][C:28]1[CH:33]=[CH:32][C:31]([F:34])=[CH:30][C:29]=1[CH:35]1[CH2:44][CH:43]([OH:45])[C:42]2[C:37](=[CH:38][CH:39]=[C:40]([OH:46])[CH:41]=2)[O:36]1>>[F:27][C:28]1[CH:33]=[CH:32][C:31]([F:34])=[CH:30][C:29]=1[CH:35]1[CH2:44][CH:43]([OH:45])[C:42]2[C:37](=[CH:38][CH:39]=[C:40]([O:46][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 179785942-(2,5-Difluorophenyl)chroman-4,6-diol

Product 1

HCID 179786322-(2,5-Difluorophenyl)-6-(5-nitropyridin-2-yloxy)chroman-4-ol

Procedure

2-(2,5-Difluorophenyl)-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 200 mg of 2-(2,5-difluorophenyl)chroman-4,6-diol (Example 14(b)). The product was purified on preparative TLC-plate covered with silica gel using toluene-ethyl acetate (4:1) as an eluant. 1H NMR (400 MHz, CDCl3) δ: 9.03 (d, 1H, J 2.8 Hz), 8.50 (dd, 1H, J 9.1, 2.8 Hz), 7-36-7.33 (m, 2H), 7.08-6.95 (m, 5H), 5.50 (d, 1H, J 11.1 Hz), 5.09 (m, 1H), 2.53 (m, 1H), 2.05 (m, 1H).

Workup

customThe product was purified on preparative

Sources & evidence

ORD record: ord-b7864bec3b264ba19fa2188ff0e6bebc
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07425568B2

Reaction notes

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