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

HRID 31257Notes

Reaction equation

HRID 31257 reaction equation
NC1C=CC(OC2C=C3C(=CC=2)OC(C2C=CC=CC=2)CC3)=NC=1.[F:25][C:26]1[CH:27]=[C:28]([CH:32]2[CH2:41][CH2:40][C:39]3[C:34](=[CH:35][CH:36]=[C:37]([O:42][C:43]4[CH:48]=[CH:47][C:46]([N+:49]([O-])=O)=[CH:45][N:44]=4)[CH:38]=3)[O:33]2)[CH:29]=[CH:30][CH:31]=1>>[F:25][C:26]1[CH:27]=[C:28]([CH:32]2[CH2:41][CH2:40][C:39]3[C:34](=[CH:35][CH:36]=[C:37]([O:42][C:43]4[N:44]=[CH:45][C:46]([NH2:49])=[CH:47][CH:48]=4)[CH:38]=3)[O:33]2)[CH:29]=[CH:30][CH:31]=1

Participants

3

Reactant 2

HCID 179784785-Amino-2-(2-phenylchroman-6-yloxy)pyridineHCID 179786432-[2-(3-Fluorophenyl)chroman-6-yloxy]-5-nitropyridine

Product 1

HCID 179786116-[2-(3-Fluorophenyl)chroman-6-yloxy]-pyridin-3-ylamine

Procedure

6-[2-(3-fluorophenyl)chroman-6-yloxy]-pyridin-3-ylamine was prepared as described for 5-amino-2-(2-phenylchroman-6-yloxy)pyridine in Example 26 starting from 2.34 g of 2-[2-(3-fluorophenyl)chroman-6-yloxy]-5-nitropyridine (Example 9(d)). 1H NMR (400 MHz, d6-DMSO) δ: 7.51 (d, 1H, J 3.0 Hz), 7.44 (m, 1H), 7.30-7.25 (m, 2H), 7.16 (m, 1H), 7.05 (dd, 1H, J 8.6, 3.0 Hz), 6.83-6.73 (m, 3H), 6.69 (d, 1H, J 8.6 Hz), 5.13 (dd, 1H, J 10.0, 3.0 Hz), 5.00 (s, 2H), 2.93 (ddd, 1H, −16.8, 10.5, 5.3 Hz), 2.68 (ddd, 1H, J −16.8, 8.0, 4.4 Hz), 2.18 (m, 1H), 1.96 (m, 1H).

Sources & evidence

ORD record
ord-6e6c825b20ff45e2adb8dcfd117a8442
Source dataset
uspto-grants-2008_09
Patent number
US07425568B2

Reaction notes

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