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

HRID 31263Notes

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

Participants

Reactant 2

HCID 17978512Orm-10103

HCID 179785532-(2-Fluorophenyl)chroman-4,6-diol

Product 1

HCID 179785852-(2-Fluorophenyl)-6-(5-nitropyridin-2-yloxy)chroman-4-ol

Procedure

2-(2-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 315 mg of 2-(2-fluorophenyl)chroman-4,6-diol (Example 19(b)). The product was recrystallised 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), 7.61 (m, 1H), 7.43 (m, 1H), 7.31-7.24 (m, 3H), 7.23 (d, 1H, J 9.1 Hz), 7.02 (dd, 1H, J 8.7, 3.1 Hz), 6.89 (d, 1H, J 8.7 Hz), 5.69 (d, 1H, J 6.3 Hz), 5.55 (d, 1H, J 11.9 Hz), 5.00 (m, 1H), 2.33 (m, 1H), 2.07 (m, 1H).

Workup

customThe product was recrystallised from a mixture of 2-propanol and acetone

Sources & evidence

ORD record: ord-bc0a8bb7d2764a19b4a37af582d5afa5
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07425568B2

Reaction notes

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