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

HRID 31194Notes

Reaction equation

HRID 31194 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][CH2:43][C:42]2[C:37](=[CH:38][CH:39]=[C:40]([OH:45])[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][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

3

Reactant 2

HCID 17978512Orm-10103HCID 179785262-(2,5-Difluorophenyl)chroman-6-ol

Product 1

HCID 179786452-[2-(2,5-Difluorophenyl)chroman-6-yloxy]-5-nitropyridine

Procedure

2-[2-(2,5-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 100 mg of 2-(2,5-difluorophenyl)chroman-6-ol. The product was recrystallised from 2-propanol. 1H NMR (400 MHz, CDCl3) δ: 9.07 (dd, 1H, J 2.8, 0.4 Hz), 8.47 (dd, 1H, J 9.1, 2.8 Hz), 7.26 (m, 1H), 7.05-6.91 (m, 6H), 5.35 (dd, 1H, J 10.3, 1.5 Hz), 3.04 (ddd, 1H, J −16.9, 11.7, 6.0 Hz), 2.82 (ddd, 1H, J −16.9, 5.2, 3.0 Hz), 2.29 (m, 1H), 2.01 (m, 1H).

Workup

  1. customThe product was recrystallised from 2-propanol

Sources & evidence

ORD record
ord-04852242727c4875b418368a8078f6da
Source dataset
uspto-grants-2008_09
Patent number
US07425568B2

Reaction notes

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