2-(3-Fluorophenyl)chroman-6-ol → 2-[2-(3-Fluorophenyl)chroman-6-yloxy]-5-nitropyridine

HRID 31176Notes

Reaction equation

HRID 31176 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([O:10][C:11]2[CH:12]=[C:13]3[C:18](=[CH:19][CH:20]=2)[O:17][CH:16]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:15][CH2:14]3)=[N:8][CH:9]=1)([O-:3])=[O:2].[F:27]C1C=C(C2CCC3C(=CC=C(O)C=3)O2)C=CC=1>>[F:27][C:25]1[CH:26]=[C:21]([CH:16]2[CH2:15][CH2:14][C:13]3[C:18](=[CH:19][CH:20]=[C:11]([O:10][C:7]4[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][N:8]=4)[CH:12]=3)[O:17]2)[CH:22]=[CH:23][CH:24]=1

Participants

3

Reactant 2

HCID 179784712-(3-Fluorophenyl)chroman-6-olHCID 17978512Orm-10103

Product 1

HCID 179786432-[2-(3-Fluorophenyl)chroman-6-yloxy]-5-nitropyridine

Procedure

2-[2-(3-Fluorophenyl)chroman-6-yloxy]-5-nitropyridine was prepared as described for 5-nitro-2-(2-phenylchroman-6-yloxy)pyridine in Example 1(b) starting from 210 mg of 2-(3-fluorophenyl)chroman-6-ol. The product was recrystallised from 2-propanol. 1H NMR (400 MHz, CDCl3) δ: 9.07 (d, 1H, J 2.8 Hz), 8.46 (dd, 1H, J 9.0, 2.8 Hz), 7.36 (m, 1H), 7.21-7.15 (m, 2H), 7.03 (m, 1H), 7.01 (d, 1H, J 9.0 Hz), 6.98 (d, 1H, J 8.6 Hz), 6.92 (dd, 1H, J 8.6, 2.7 Hz), 6.90 (d, 1H, J 2.7 Hz), 5.09 (dd, 1H, J 10.3, 2.4 Hz), 3.01 (ddd, 1H, J −16.9, 11.4, 6.0 Hz), 2.82 (ddd, 1H, J −16.9, 5.1, 3.2 Hz), 2.24 (m, 1H), 2.09 (m, 1H).

Workup

  1. customThe product was recrystallised from 2-propanol

Sources & evidence

ORD record
ord-d9af3696664740a5a66296890a50abbf
Source dataset
uspto-grants-2008_09
Patent number
US07425568B2

Reaction notes

Loading…