5-Amino-2-(2-phenylchroman-6-yloxy)pyridine → 6-(5-Aminopyridin-2-yloxy)-2-(4-methoxyphenyl)chroman-4-ol

HRID 31332Notes

Reaction equation

HRID 31332 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][C:30]([CH:33]2[CH2:42][CH:41]([OH:43])[C:40]3[C:35](=[CH:36][CH:37]=[C:38]([O:44][C:45]4[CH:50]=[CH:49][C:48]([N+:51]([O-])=O)=[CH:47][N:46]=4)[CH:39]=3)[O:34]2)=[CH:29][CH:28]=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:30]2[CH:31]=[CH:32][C:27]([O:26][CH3:25])=[CH:28][CH:29]=2)[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 179786092-(4-Methoxyphenyl)-6-(5-nitropyridin-2-yloxy)chroman-4-ol

Product 1

HCID 179785766-(5-Aminopyridin-2-yloxy)-2-(4-methoxyphenyl)chroman-4-ol

Reagents, catalysts & solvents 1

HCID 23994ZincCatalyst

Procedure

6-(5-Aminopyridin-2-yloxy)-2-(4-methoxyphenyl)chroman-4-ol was prepared as described for 5-amino-2-(2-phenylchroman-6-yloxy)pyridine in Example 26 using 105 mg 2-(4-methoxyphenyl)-6-(5-nitropyridin-2-yloxy)chroman-4-ol (Example 94(c)) and 348 mg of Zn. 1H NMR (400 MHz, d6-DMSO) δ: 7.52 (d, 1H, J 3.0 Hz), 7.38 (d, 2H, J 8.8 Hz), 7.06 (dd, 1H, J 8.7, 3.0 Hz), 7.04 (d, 1H, J 2.9 Hz), 6.96 (d, 2H, J 8.8 Hz), 6.77 (dd, 1H, J 8.7, 2.9 Hz), 6.72 (d, 1H, J 8.7 Hz), 6.70 (d, 1H, J 8.6 Hz), 5.52 (d, 1H, J 6.6 Hz), 5.15 (d, 1H, J 10.7 Hz), 5.01 (s, 2H), 4.87-4.93 (m, 1H), 3.77 (s, 3H), 2.22-2.26 (m, 1H), 1.90-1.99 (m, 1H).

Sources & evidence

ORD record
ord-5c768b4b50814ae480cb38152c15bdba
Source dataset
uspto-grants-2008_09
Patent number
US07425568B2

Reaction notes

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