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

HRID 31288Notes

Reaction equation

HRID 31288 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=CC=CC=1C1CCC2C(=CC=C(O)C=2)O1>>[Cl:27][C:26]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[CH:16]1[CH2:15][CH2:14][C:13]2[C:18](=[CH:19][CH:20]=[C:11]([O:10][C:7]3[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][N:8]=3)[CH:12]=2)[O:17]1

Participants

3

Reactant 2

HCID 17978512Orm-10103HCID 179786292-(2-Chlorophenyl)chroman-6-ol

Product 1

HCID 179785272-[2-(2-Chlorophenyl)chroman-6-yloxy]-5-nitropyridine

Procedure

2-[2-(2-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 485 mg of 2-(2-chlorophenyl)chroman-6-ol. 1H NMR (400 MHz, d6-DMSO) δ: 9.04 (d, 1H, J 2.9, 0.5 Hz), 8.60 (dd, 1H, J 9.1, 2.9 Hz), 7.62 (dd, 1H, J 7.5, 1.8 Hz), 7.51 (dd, 1H, J 7.6, 1.7 Hz), 7.45-7.40 (m, 2H), 7.21 (dd, 1H, J 9.1, 0.5 Hz), 7.04 (d, 1H, J 2.7 Hz), 6.99 (dd, 1H, J 8.8, 2.7 Hz), 6.94 (d, 1H, 8.8 Hz), 5.40 (dd, 1H, J 10.4, 2.1 Hz), 3.04 (m, 1H), 2.80 (m, 1H), 2.24 (m, 1H), 1.95 (m, 1H).

Sources & evidence

ORD record
ord-9a41de9d282c48f1a81301ae65ffa5ec
Source dataset
uspto-grants-2008_09
Patent number
US07425568B2

Reaction notes

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