5-Amino-2-(2-phenylchroman-6-yloxy)pyridine → HCID 69255747, compound

HRID 31335Notes

Reaction equation

HRID 31335 reaction equation
NC1C=CC(OC2C=C3C(=CC=2)OC(C2C=CC=CC=2)CC3)=NC=1.[CH3:25][O:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[CH:33]1[CH2:42][CH:41]([OH:43])[C:40]2[C:35](=[CH:36][CH:37]=[C:38]([O:44][C:45]3[CH:50]=[CH:49][C:48]([N+:51]([O-])=O)=[CH:47][N:46]=3)[CH:39]=2)[O:34]1>[Zn]>[NH2:51][C:48]1[CH:49]=[CH:50][C:45]([O:44][C:38]2[CH:39]=[C:40]3[C:35](=[CH:36][CH:37]=2)[O:34][CH:33]([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=2[O:26][CH3:25])[CH2:42][CH:41]3[OH:43])=[N:46][CH:47]=1

Participants

4

Reactant 2

HCID 179784785-Amino-2-(2-phenylchroman-6-yloxy)pyridineHCID 179785402-(2-Methoxyphenyl)-6-(5-nitropyridin-2-yloxy)chroman-4-ol

Product 1

HCID 69255747HCID 69255747, compound

Reagents, catalysts & solvents 1

HCID 23994ZincCatalyst

Procedure

6-(5-Aminopyridin-2-yloxy)-2-(2-methoxyphenyl)chroman-4-ol was prepared as described for 5-amino-2-(2-phenylchroman-6-yloxy)pyridine in Example 26 using 79 mg 2-(2-methoxyphenyl)-6-(5-nitropyridin-2-yloxy)chroman-4-ol (Example 97(c)) and 262 mg of Zn. 1H NMR (400 MHz, d6-DMSO) δ: 7.52 (d, 1H, J 2.9 Hz), 7.47 (dd, 1H, J 7.5, 1.6 Hz), 7.33 (dt, 1H, J 8.5, 7.4, 1.6 Hz), 7.06 (d, 1H, J 2.8 Hz), 7.03-7.05 (m, 2H), 7.01 (d, 1H, J 7.4 Hz), 6.79 (dd, 1H, J 8.6, 2.8 Hz), 6.75 (d, 1H, J 8.7 Hz), 6.71 (d, 1H, J 8.6 Hz), 5.52 (d, 1H, J 6.5 Hz), 5.44 (d, 1H, J 10.5 Hz), 5.01 (s, 2H), 4.86-4.92 (m, 1H), 3.83 (s, 3H), 2.27-2.32 (m, 1H), 1.80-1.88 (m, 1H).

Sources & evidence

ORD record
ord-7f4f9ecd055145d6b87c29cc2c6b31d4
Source dataset
uspto-grants-2008_09
Patent number
US07425568B2

Reaction notes

Loading…