5-Amino-2-(2-phenylchroman-6-yloxy)pyridine → 6-[2-(4-Aminophenyl)chroman-6-yloxy]-pyridin-3-ylamine

HRID 31321Notes

Reaction equation

HRID 31321 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][C:48]([N+:51]([O-])=O)=[CH:47][CH:46]=2)[CH2:39][CH2:38]3)=[N:32][CH:33]=1)([O-])=O>[Zn]>[NH2:51][C:48]1[CH:49]=[CH:50][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:46][CH:47]=1

Participants

4

Reactant 2

HCID 179784785-Amino-2-(2-phenylchroman-6-yloxy)pyridineHCID 179784845-Nitro-2-[2-(4-nitrophenyl)chroman-6-yloxy]pyridine

Product 1

HCID 179784746-[2-(4-Aminophenyl)chroman-6-yloxy]-pyridin-3-ylamine

Reagents, catalysts & solvents 1

HCID 23994ZincCatalyst

Procedure

6-[2-(4-Aminophenyl)chroman-6-yloxy]-pyridin-3-ylamine was prepared as described for 5-amino-2-(2-phenylchroman-6-yloxy)pyridine in Example 26 using 100 mg 5-nitro-2-[2-(4-nitrophenyl)chroman-6-yloxy]pyridine (Example 87(d)) and 665 mg of Zn. 1H NMR (400 MHz, d6-DMSO) δ: 7.50 (d, 1H, J 2.9 Hz), 7.07 (d, 2H, 8.4 Hz), 7.04 (dd, 1H, J 8.6, 2.9 Hz), 6.71 (s, 3H), 6.68 (d, 1H, J 8.6 Hz), 6.56 (d, 2H, J 8.4 Hz), 5.07 (s, 2H), 4.99 (s, 2H), 4.84 (dd, 1H, J 9.7, 2.3 Hz), 2.86-2.95 (m, 1H), 2.66-2.71 (m, 1H), 1.95-2.05 (m, 2H).

Sources & evidence

ORD record
ord-8afce6a855e349d79cceacfb9d20aac0
Source dataset
uspto-grants-2008_09
Patent number
US07425568B2

Reaction notes

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