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

HRID 31198Notes

Reaction equation

HRID 31198 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].[Br:27]C1C=C(C2CCC3C(=CC=C(O)C=3)O2)C=CC=1>>[Br: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

3

Reactant 2

HCID 17978512Orm-10103HCID 179785982-(3-Bromophenyl)chroman-6-ol

Product 1

HCID 179786532-[2-(3-Bromophenyl)chroman-6-yloxy]-5-nitropyridine

Procedure

2-[2-(3-Bromophenyl)chroman-6-yloxy]-5-nitropyridine was prepared as described for 5-nitro-2-(2-phenylchroman-6-yloxy)pyridine in Example 1(b) starting from 339 mg of 2-(3-bromophenyl)chroman-6-ol. The product was filtered through silica gel using toluene-ethyl acetate as an eluant and then crystallised from 2-propanol. 1H NMR (400 MHz, CDCl3) δ: 9.04 (d, 1H, J 2.9 Hz), 8.60 (dd, 1H, J 9.2, 2.9 Hz), 7.66 (bs, 1H), 7.55 (m, 1H), 7.48 (m, 1H), 7.39 (m, 1H), 7.20 (d, 1H, J 9.2 Hz), 7.01-6.93 (m, 3H), 5.17 (dd, 1H, J 10.1, 2.2 Hz), 2.97 (m, 1H), 2.72 (m, 1H), 2.20 (m, 1H), 2.00 (m, 1H).

Workup

  1. filtrationThe product was filtered through silica gel
  2. customcrystallised from 2-propanol

Sources & evidence

ORD record
ord-090e122d4d7343e69fe7fdb748ec7fc1
Source dataset
uspto-grants-2008_09
Patent number
US07425568B2

Reaction notes

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