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

HRID 31281Notes

Reaction equation

HRID 31281 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]=[C:32]([F: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>>[F:27][C:28]1[CH:33]=[C:32]([F: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

3

Reactant 2

HCID 17978512Orm-10103HCID 17978525HCID 17978525, compound

Product 1

HCID 179784562-[2-(2,4-Difluorophenyl)chroman-6-yloxy]-5-nitropyridine

Procedure

2-[2-(2,4-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 720 mg of 2-(2,4-difluorophenyl)chroman-6ol. 1H NMR (400 MHz, d6-DMSO) δ: 9.04 (d, 1H, J 3.0 Hz), 8.60 (dd, 1H, J 9.0, 3.0 Hz), 7.61 (m, 1H), 7.31 (m, 1H), 7.21 (d, 1H, 9.0 Hz), 7.17 (m, 1H), 7.02 (d, 1H, J 2.9 Hz), 6.97 (dd, 1H, J 8.9, 2.9 Hz), 6.91 (d, 1H, 8.9 Hz), 5.34 (dd, 1H, J 9.9, 2.0 Hz), 3.03 (m, 1H), 2.78 (m, 1H), 2.17 (m, 1H), 2.07 (m, 1H).

Sources & evidence

ORD record
ord-bbba28a5014b4839b48c75d8a5f2f791
Source dataset
uspto-grants-2008_09
Patent number
US07425568B2

Reaction notes

Loading…