2-(4-Fluorophenyl)chroman-6-ol → 2-[2-(4-Fluorophenyl)chroman-6-yloxy]-5-nitropyridine

HRID 1455014Notes

Reaction equation

HRID 1455014 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=CC(C2CCC3C(=CC=C(O)C=3)O2)=CC=1>>[F:27][C:24]1[CH:23]=[CH:22][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:26][CH:25]=1

Participants

3

Reactant 2

HCID 179784812-(4-Fluorophenyl)chroman-6-olHCID 17978512Orm-10103

Product 1

HCID 179785292-[2-(4-Fluorophenyl)chroman-6-yloxy]-5-nitropyridine

Procedure

2-[2-(4-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 160 mg of 2-(4-fluorophenyl)chroman-6-ol. 1H NMR (400 MHz, d6-DMSO) δ: 9.04 (dd, 1H, J 2.9, 0.4 Hz), 8.60 (dd, 1H, J 9.1, 2.9 Hz), 7.51 (m, 2H), 7.24 (m, 1H), 7.20 (dd, 1H, J 9.1, 0.4 Hz), 7.01 (d, 1H, J 2.8 Hz), 6.96 (dd, 1H, J 8.7, 2.8 Hz) 6.91 (d, 1H, 8.7 Hz), 5.15 (dd, 1H, J 10.3, 2.2 Hz), 2.94 (m, 1H), 2.76 (m, 1H) 2.17 (m, 1H), 2.01 (m, 1H).

Sources & evidence

ORD record
ord-5b119d0e05fe47bb8732dc171482574a
Source dataset
uspto-grants-2009_01
Patent number
US07482340B2

Reaction notes

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