3-(3-Fluorophenyl)chroman-7-ol → 2-[3-(3-Fluorophenyl)chroman-7-yloxy]-5-nitropyridine

HRID 31309Notes

Reaction equation

HRID 31309 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:34]2[CH2:43][C:42]3[C:37](=[CH:38][C:39]([OH:44])=[CH:40][CH:41]=3)[O:36][CH2:35]2)[CH:31]=[CH:32][CH:33]=1>>[F:27][C:28]1[CH:29]=[C:30]([CH:34]2[CH2:43][C:42]3[C:37](=[CH:38][C:39]([O:44][C:7]4[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][N:8]=4)=[CH:40][CH:41]=3)[O:36][CH2:35]2)[CH:31]=[CH:32][CH:33]=1

Participants

3

Reactant 2

HCID 179784803-(3-Fluorophenyl)chroman-7-olHCID 17978512Orm-10103

Product 1

HCID 179786252-[3-(3-Fluorophenyl)chroman-7-yloxy]-5-nitropyridine

Procedure

2-[3-(3-Fluorophenyl)chroman-7-yloxy]-5-nitropyridine was prepared as described for 5-nitro-2-(2-phenylchroman-6-yloxy)pyridine in Example 1(b) using 125 mg of 3-(3-fluorophenyl)-chroman-7-ol. The product was recrystallised from ethanol. 1H NMR (400 MHz, CDCl3) δ: 9.07 (d, 1H, J 2.8 Hz), 8.47 (dd, 1H, J 9.0, 2.8 Hz), 7.33 (m, 1H), 7.16 (d, 1H, J 8.9 Hz), 6.95-7.06 (m, 4H), 6.69-6.71 (m, 2H), 4.38 (dd, 1H, J 10.6, 4.3 Hz), 4.06 (t, 1H, 10.6 Hz), 3.30 (m, 1H), 3.06 (m, 2H).

Workup

  1. customThe product was recrystallised from ethanol

Sources & evidence

ORD record
ord-2b6a1d15fccc4632b262138acc383e19
Source dataset
uspto-grants-2008_09
Patent number
US07425568B2

Reaction notes

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