Orm-10103 → 2-[2-(3-Chlorophenyl)chroman-6-yloxy]-5-nitropyridine

HRID 31186Notes

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].[Cl:27]C1C=C(C2CCC3C(=CC=C(O)C=3)O2)C=CC=1>>[Cl: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

Reactant 2

HCID 17978512Orm-10103

HCID 179786272-(3-Chlorophenyl)chroman-6-ol

Product 1

HCID 179784582-[2-(3-Chlorophenyl)chroman-6-yloxy]-5-nitropyridine

Procedure

2-[2-(3-Chlorophenyl)chroman-6-yloxy]-5-nitropyridine was prepared as described for 5-nitro-2-(2-phenylchroman-6-yloxy)pyridine in Example 1(b) starting from 590 mg of 2-(3-chlorophenyl)chroman-6-ol. The product was recrystallised from a 3:1 mixture of 2-propanol and ethyl acetate. 1H NMR (400 MHz, CDCl3) δ: 9.04 (d, 1H, J 2.9 Hz), 8.60 (dd, 1H, J 9.0, 2.9 Hz), 7.53 (s, 1H), 7.467-7.42 (m, 3H), 7.20 (d, 1H, J 9.0 Hz), 7.00 (dd, 1H, J 8.7, 2.7 Hz), 6.97 (d, 1H, J 2.7 Hz), 6.94 (d, 1H, J 8.7 Hz), 5.18 (dd, 1H, J 10.2, 2.2 Hz), 2.97 (ddd, 1H, J −17.0, 11.5, 5.9 Hz), 2.83 (ddd, 1H, J −17.0, 8.1, 4.5 Hz), 2.21 (m, 1H), 2.00 (m, 1H).

Workup

customThe product was recrystallised from a 3:1 mixture of 2-propanol and ethyl acetate

Sources & evidence

ORD record: ord-6645e68685bd4955ab1dd0e5ba1e0df7
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07425568B2

Reaction notes

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