5-Amino-2-(2-phenylchroman-6-yloxy)pyridine → HCID 17978497, compound

HRID 31339Notes

Reaction equation

HRID 31339 reaction equation
NC1C=CC(OC2C=C3C(=CC=2)OC(C2C=CC=CC=2)CC3)=NC=1.[CH3:25][O:26][C:27]1[CH:28]=[C:29]([CH:33]2[CH2:42][CH2:41][C:40]3[C:35](=[CH:36][CH:37]=[C:38]([O:43][C:44]4[CH:49]=[CH:48][C:47]([N+:50]([O-])=O)=[CH:46][N:45]=4)[CH:39]=3)[O:34]2)[CH:30]=[CH:31][CH:32]=1>[Zn]>[CH3:25][O:26][C:27]1[CH:28]=[C:29]([CH:33]2[CH2:42][CH2:41][C:40]3[C:35](=[CH:36][CH:37]=[C:38]([O:43][C:44]4[N:45]=[CH:46][C:47]([NH2:50])=[CH:48][CH:49]=4)[CH:39]=3)[O:34]2)[CH:30]=[CH:31][CH:32]=1

Participants

4

Reactant 2

HCID 179784785-Amino-2-(2-phenylchroman-6-yloxy)pyridineHCID 179786242-[2-(3-Methoxyphenyl)chroman-6-yloxy]-5-nitropyridine

Product 1

HCID 17978497HCID 17978497, compound

Reagents, catalysts & solvents 1

HCID 23994ZincCatalyst

Procedure

6-[2-(3-Methoxyphenyl)chroman-6-yloxy]pyridin-3-ylamine was prepared as described for 5-amino-2-(2-phenylchroman-6-yloxy)pyridine in Example 26 using 300 mg 2-[2-(3-methoxyphenyl)chroman-6-yloxy]-5-nitropyridine (Example 99(d)) and 1.0 g of Zn. H NMR (400 MHz, d6-DMSO) δ: 7.51 (d, 1H, J 3.0 Hz), 7.31 (t, 1H, J 15.8, 7.9 Hz), 7.04 (dd, 1H, J 8.7, 3.0 Hz), 6.99-7.02 (m, 1H), 6.99 (d, 1H, J 2.6 Hz), 6.90 (dd, 1H, J 8.9, 2.6 Hz), 6.79-6.81 (m, 1H), 6.72-6.74 (m, 2H), 6.69 (d, 1H, J 8.9 Hz), 5.06 (dd, 1H, J 9.9, 2.2 Hz), 4.50 (s, 2H), 3.77 (s, 3H), 2.88-2.95 (m, 1H), 2.66-2.71 (m, 1H), 2.12-2.17 (m, 1H), 1.94-2.00 (m, 1H).

Sources & evidence

ORD record
ord-52d44ec6477e4bc58d2fe54c2efa3971
Source dataset
uspto-grants-2008_09
Patent number
US07425568B2

Reaction notes

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