Orm-10103 → 6-(5-Nitropyridin-2-yloxy)-2-(2-trifluoromethylphenyl)chroman-4-ol

HRID 31304Notes

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]([F:48])([F:47])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=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>>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([O:46][C:40]2[CH:41]=[C:42]3[C:37](=[CH:38][CH:39]=2)[O:36][CH:35]([C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=2[C:28]([F:27])([F:47])[F:48])[CH2:44][CH:43]3[OH:45])=[N:8][CH:9]=1)([O-:3])=[O:2]

Participants

Reactant 2

HCID 17978512Orm-10103

HCID 179786182-(2-Trifluoromethylphenyl)chroman-4,6-diol

Product 1

HCID 179785076-(5-Nitropyridin-2-yloxy)-2-(2-trifluoromethylphenyl)chroman-4-ol

Procedure

6-(5-Nitropyridin-2-yloxy)-2-(2-trifluoromethylphenyl)chroman-4-ol was prepared as described for 5-nitro-2-(2-phenylchroman-6-yloxy)pyridine in Example 1(b) starting from 350 mg of 2-(2-trifluoromethylphenyl)chroman-4,6-diol. 1H NMR (400 MHz, d6-DMSO) δ: 9.04 (d, 1H, J 2.8 Hz), 8.62 (dd, 1H, J 9.1, 2.8 Hz), 7.89 (m, 1H), 7.82-7.78 (m, 2H), 7.62 (m, 1H), 7.28 (d, 1H, J 2.7 Hz), 7.24 (d, 1H, 9.1 Hz), 7.04 (dd, 1H, J 8.7, 2.7 Hz), 6.90 (d, 1H, J 8.7 Hz), 5.7 (bs, 1H), 5.38 (d, 1H, J 11.6 Hz), 5.01 (m, 1H), 2.29 (m, 1H), 2.05 (m, 1H).

Sources & evidence

ORD record: ord-a62561cccc764153bf176a4d713d1df8
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07425568B2

Reaction notes

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