Orm-10103 → 2-[2-(3,5-Difluorophenyl)chroman-6-yloxy]-5-nitropyridine

HRID 31190Notes

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

Participants

Reactant 2

HCID 17978512Orm-10103

HCID 179785282-(3,5-Difluorophenyl)chroman-6-ol

Product 1

HCID 179786192-[2-(3,5-Difluorophenyl)chroman-6-yloxy]-5-nitropyridine

Procedure

2-[2-(3,5-Difluorophenyl)chroman-6-yloxy]-5-nitropyridine was prepared as described for 5-nitro-2-(2-phenylchroman-6-yloxy)pyridine in Example 1(b) starting from 340 mg of 2-(3,5-difluorophenyl)chroman-6-ol. The product was purified on preparative TLC-plate covered with silica gel using toluene-ethyl acetate as an eluant and then crystallised from 2-propanol. 1H NMR (400 MHz, d6-DMSO) δ:9.04 (d, 1H, J 2.9 Hz), 8.60 (dd, 1H, J 9.1, 2.9 Hz), 7.23-7.19 (m, 4H), 7.01-6.95 (m, 3H), 5.18 (dd, 1H, J 10.0, 2.1 Hz), 2.97 (ddd, 1H, J −16.9, 10.9, 5.7 Hz), 2.76 (ddd, 1H, J −16.9, 8.4, 4.7 Hz), 2.22 (m, 1H), 1.99 (m, 1H).

Workup

customThe product was purified on preparative
customcrystallised from 2-propanol

Sources & evidence

ORD record: ord-027a6263d4f1435384292b47cd9f6232
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07425568B2

Reaction notes

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