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

HRID 31325Notes

Reaction equation

HRID 31325 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][C:46]=2[N+:51]([O-])=O)[CH2:39][CH2:38]3)=[N:32][CH:33]=1)([O-])=O>[Zn]>[NH2:51][C:46]1[CH:47]=[CH:48][CH:49]=[CH:50][C:45]=1[CH:40]1[CH2:39][CH2:38][C:37]2[C:42](=[CH:43][CH:44]=[C:35]([O:34][C:31]3[N:32]=[CH:33][C:28]([NH2:25])=[CH:29][CH:30]=3)[CH:36]=2)[O:41]1

Participants

4

Reactant 2

HCID 179784785-Amino-2-(2-phenylchroman-6-yloxy)pyridineHCID 179785625-Nitro-2-[2-(2-nitrophenyl)chroman-6-yloxy]pyridine

Product 1

HCID 179784576-[2-(2-Aminophenyl)chroman-6-yloxy]-pyridin-3-ylamine

Reagents, catalysts & solvents 1

HCID 23994ZincCatalyst

Procedure

6-[2-(2-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-(2-nitrophenyl)chroman-6-yloxy]pyridine (Example 89(d)) and 700 mg of Zn. 1H NMR (300 MHz, d6-DMSO) δ: 7.51 (d, 1H, J 2.9 Hz), 7.15-7.18 (m, 1H), 7.05 (dd, 1H, J 8.6, 2.9 Hz), 6.98-7.00 (m, 1H), 6.77 (d, 1H, J 8.6 Hz), 6.73-6.75 (m, 2H), 6.66-6.71 (m, 2H), 6.56-6.61 (m, 1H), 5.11 (dd, 1H, J 10.4, 2.0 Hz), 5.01 (s, 2H), 4.99 (s, 2H), 2.94-2.99 (m, 1H), 2.66-2.74 (m, 1H), 2.06-2.13 (m, 1H), 1.88-1.95 (m, 1H).

Sources & evidence

ORD record
ord-d8349279b39d474eae09bd8e894b1d1d
Source dataset
uspto-grants-2008_09
Patent number
US07425568B2

Reaction notes

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