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

HRID 31254Notes

Reaction equation

HRID 31254 reaction equation
NC1C=CC(OC2C=C3C(=CC=2)OC(C2C=CC=CC=2)CC3)=NC=1.[F:25][C:26]1[CH:31]=[CH:30][C:29]([F:32])=[CH:28][C:27]=1[CH:33]1[CH2:42][CH2:41][C:40]2[C:35](=[CH:36][CH:37]=[C:38]([O:43][C:44]3[CH:49]=[CH:48][C:47]([N+:50]([O-])=O)=[CH:46][N:45]=3)[CH:39]=2)[O:34]1>>[F:25][C:26]1[CH:31]=[CH:30][C:29]([F:32])=[CH:28][C:27]=1[CH:33]1[CH2:42][CH2:41][C:40]2[C:35](=[CH:36][CH:37]=[C:38]([O:43][C:44]3[N:45]=[CH:46][C:47]([NH2:50])=[CH:48][CH:49]=3)[CH:39]=2)[O:34]1

Participants

3

Reactant 2

HCID 179784785-Amino-2-(2-phenylchroman-6-yloxy)pyridineHCID 179786452-[2-(2,5-Difluorophenyl)chroman-6-yloxy]-5-nitropyridine

Product 1

HCID 179784476-[2-(2,5-Difluorophenyl)chroman-6-yloxy]-pyridin-3-ylamine

Procedure

6-[2-(2,5-Difluorophenyl)chroman-6-yloxy]-pyridin-3-ylamine was prepared as described for 5-amino-2-(2-phenylchroman-6-yloxy)pyridine in Example 26 starting from 830 mg of 2-[2-(2,5-Difluorophenyl)chroman-6-yloxy]-5-nitropyridine (Example 14(d)). 1H NMR (300 MHz, d6-DMSO) δ: 7.51 (d, 1H, J 2.9 Hz), 7.36-7.25 (m, 3H), 7.05 (dd, 1H, J 8.6, 2.9 Hz), 6.84-6.68 (m, 4H), 5.29 (d, 1H, J 8.6), 4.99 (s, 2H), 2.96 (m, 1H), 2.72 (m, 1H), 2.14 (m, 1H), 2.01 (m, 1H).

Sources & evidence

ORD record
ord-3277979ba2214cef9cb59afe151478f9
Source dataset
uspto-grants-2008_09
Patent number
US07425568B2

Reaction notes

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