5-Amino-2-(2-phenylchroman-6-yloxy)pyridine → 6-[2-(3-Aminophenyl)chroman-6-yloxy]-pyridin-3-ylamine

HRID 31329Notes

Reaction equation

HRID 31329 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]=[C:47]([N+:51]([O-])=O)[CH:46]=2)[CH2:39][CH2:38]3)=[N:32][CH:33]=1)([O-])=O>[Zn]>[NH2:51][C:47]1[CH:46]=[C:45]([CH:40]2[CH2:39][CH2:38][C:37]3[C:42](=[CH:43][CH:44]=[C:35]([O:34][C:31]4[N:32]=[CH:33][C:28]([NH2:25])=[CH:29][CH:30]=4)[CH:36]=3)[O:41]2)[CH:50]=[CH:49][CH:48]=1

Participants

4

Reactant 2

HCID 179784785-Amino-2-(2-phenylchroman-6-yloxy)pyridineHCID 179786035-Nitro-2-[2-(3-nitrophenyl)chroman-6-yloxy]pyridine

Product 1

HCID 179785876-[2-(3-Aminophenyl)chroman-6-yloxy]-pyridin-3-ylamine

Reagents, catalysts & solvents 1

HCID 23994ZincCatalyst

Procedure

6-[2-(3-Aminophenyl)chroman-6-yloxy]-pyridin-3-ylamine was prepared as described for 5-amino-2-(2-phenylchroman-6-yloxy)pyridine in Example 26 using 150 mg 5-nitro-2-[2-(3-nitrophenyl)chroman-6-yloxy]pyridine (Example 92(d)) and 997 mg of Zn. 1H NMR (300 MHz, d6-DMSO) δ: 7.51 (d, 1H, J 2.8 Hz), 7.05 (dd, 1H, J 8.6, 2.8 Hz), 7.01 (t, 1H, J 15.4, 7.7 Hz), 6.70-6.78 (m, 3H), 6.68 (d, 1H, J 8.6 Hz), 6.63 (s, 1H), 6.54 (d, 1H, J 7.7 Hz), 6.50 (d, 1H, J 8.6 Hz), 5.06 (s, 2H), 4.98 (s, 2H), 4.90 (dd, 1H, J 10.0, 2.2 Hz), 2.85-2.96 (m, 1H), 2.62-2.74 (m, 1H), 2.05-2.11 (m, 1H), 1.89-1.95 (m, 1H).

Sources & evidence

ORD record
ord-176cdf2c73964d758955d5d50dd6158f
Source dataset
uspto-grants-2008_09
Patent number
US07425568B2

Reaction notes

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