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

HRID 31273Notes

Reaction equation

HRID 31273 reaction equation
NC1C=CC(OC2C=C3C(=CC=2)OC(C2C=CC=CC=2)CC3)=NC=1.[F:25][C:26]([F:54])([F:53])[C:27]1[CH:32]=[CH:31][C:30]([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:29][CH:28]=1>>[F:54][C:26]([F:25])([F:53])[C:27]1[CH:32]=[CH:31][C:30]([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:29][CH:28]=1

Participants

3

Reactant 2

HCID 179784785-Amino-2-(2-phenylchroman-6-yloxy)pyridineHCID 179785792-[2-(4-Trifluoromethylphenyl)chroman-6-yloxy]-5-nitropyridine

Product 1

HCID 179784946-[2-(4-Trifluoromethylphenyl)chroman-6-yloxy]pyridin-3-ylamine

Procedure

6-[2-(4-Trifluoromethylphenyl)chroman-6-yloxy]pyridin-3-ylamine was prepared as described for 5-amino-2-(2-phenylchroman-6-yloxy)pyridine in Example 26 starting from 275 mg of 2-[2-(4-trifluoromethylphenyl)chroman-6-yloxy]-5-nitropyridine (Example 64(d)). 1H NMR (400 MHz, d6-DMSO) δ: 7.78 (d, 2H, J 8.4 Hz), 7.68 (d, 2H, J 8.4 Hz), 7.52 (dd, 1H, J 2.9, 0.5 Hz), 7.06 (dd, 1H, 8.6, 2.9 Hz) 6.84 (m, 1H), 6.77-6.75 (m, 2H), 6.70 (dd, 1H, J 8.6, 0.5 Hz), 5.23 (dd, 1H, J 10.0, 2.0 Hz), 5.01 (s, 2H), 2.95 (ddd, 1H, −16.8, 11.1, 5.9 Hz), 2.69 (ddd, 1H, J −16.8, 8.5, 4.8 Hz), 2.21 (m, 1H), 1.97 (m, 1H).

Sources & evidence

ORD record
ord-b8bc5c64db284df89a2c9403ccc4d339
Source dataset
uspto-grants-2008_09
Patent number
US07425568B2

Reaction notes

Loading…