5-Amino-2-(2-phenylchroman-6-yloxy)pyridine → 6-(5-Aminopyridin-2-yloxy)-2-phenylchroman-4-one

HRID 31258Notes

Reaction equation

HRID 31258 reaction equation
NC1C=CC(OC2C=C3C(=CC=2)OC(C2C=CC=CC=2)CC3)=NC=1.[N+:25]([C:28]1[CH:29]=[CH:30][C:31]([O:34][C:35]2[CH:36]=[C:37]3[C:42](=[CH:43][CH:44]=2)[O:41][CH:40]([C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)[CH2:39][C:38]3=[O:51])=[N:32][CH:33]=1)([O-])=O>>[NH2:25][C:28]1[CH:29]=[CH:30][C:31]([O:34][C:35]2[CH:36]=[C:37]3[C:42](=[CH:43][CH:44]=2)[O:41][CH:40]([C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)[CH2:39][C:38]3=[O:51])=[N:32][CH:33]=1

Participants

3

Reactant 2

HCID 179784785-Amino-2-(2-phenylchroman-6-yloxy)pyridineHCID 179785156-(5-Nitropyridin-2-yloxy)-2-phenylchroman-4-one

Product 1

HCID 179785616-(5-Aminopyridin-2-yloxy)-2-phenylchroman-4-one

Procedure

6-(5-Aminopyridin-2-yloxy)-2-phenylchroman-4-one was prepared as described for 5-amino-2-(2-phenylchroman-6-yloxy)pyridine in Example 26 starting from 100 mg of 6-(5-nitropyridin-2-yloxy)-2-phenylchroman-4-one (Example 6). 1H NMR (400 MHz, CD3OD) δ: 7.62 (d, 1H, J 3.0 Hz), 7.51-7.49 (m, 2H), 7.42-7.33 (m, 3H), 7.25-7.18 (m, 3H), 7.06 (d, 1H, J 8.8 Hz), 6.76 (d, 1H, J 8.6Hz), 5.50 (dd, 1H, J 13.0, 2.9 Hz), 3.08 (dd, 1H, −17.0, 13.0 Hz), 2.82 (dd, 1H, J −17.0, 2.9 Hz).

Sources & evidence

ORD record
ord-e4b090d0a6064c88aa08a8604c024331
Source dataset
uspto-grants-2008_09
Patent number
US07425568B2

Reaction notes

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