Orm-10103 → 2-(3-Fluorophenyl)-6-(5-nitropyridin-2-yloxy)chroman-4-ol

HRID 31265Notes

Reaction equation

HRID 31265 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][CH:42]([OH:44])[C:41]3[C:36](=[CH:37][CH:38]=[C:39]([OH:45])[CH:40]=3)[O:35]2)[CH:31]=[CH:32][CH:33]=1>>[F:27][C:28]1[CH:29]=[C:30]([CH:34]2[CH2:43][CH:42]([OH:44])[C:41]3[C:36](=[CH:37][CH:38]=[C:39]([O:45][C:7]4[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][N:8]=4)[CH:40]=3)[O:35]2)[CH:31]=[CH:32][CH:33]=1

Participants

3

Reactant 2

HCID 17978512Orm-10103HCID 179786382-(3-Fluorophenyl)chroman-4,6-diol

Product 1

HCID 179786402-(3-Fluorophenyl)-6-(5-nitropyridin-2-yloxy)chroman-4-ol

Procedure

2-(3-Fluorophenyl)-6-(5-nitropyridin-2-yloxy)chroman-4-ol was prepared as described for 5-nitro-2-(2-phenylchroman-6-yloxy)pyridine in Example 1(b) starting from 890 mg of 2-(3-fluorophenyl)chroman-4,6-diol (Example 9(b)). The product was purified by column chromatography using gradient elution with ethyl acetate-heptane (20%→33%) and then crystallised from a mixture of 2-propanol and acetone. 1H NMR (400 MHz, d6-DMSO) δ: 9.04 (d, 1H, J 2.9 Hz), 8.61 (dd, 1H, J 9.1, 2.9 Hz), 7.48 (m, 1H), 7.35-7.31 (m, 2H), 7.26-7.19 (m, 3H), 7.02 (dd, 1H, J 8.8, 2.9 Hz), 6.91 (d, 1H, J 8.8 Hz), 5.67 (d, 1H, J 6.4 Hz), 5.34 (d, 1H, J 10.4 Hz), 4.98 (m, 1H), 2.36 (m, 1H), 1.99 (m, 1H).

Workup

  1. customThe product was purified by column chromatography
  2. washelution with ethyl acetate-heptane (20%→33%)
  3. customcrystallised from a mixture of 2-propanol and acetone

Sources & evidence

ORD record
ord-5baf8785dc644509bc845920d9b334cf
Source dataset
uspto-grants-2008_09
Patent number
US07425568B2

Reaction notes

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