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

HRID 31294Notes

Reaction equation

HRID 31294 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]([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:28][CH:27]=1>>[F:25][C:26]1[CH:31]=[CH:30][C:29]([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:28][CH:27]=1

Participants

3

Reactant 2

HCID 179784785-Amino-2-(2-phenylchroman-6-yloxy)pyridineHCID 179785292-[2-(4-Fluorophenyl)chroman-6-yloxy]-5-nitropyridine

Product 1

HCID 179785666-[2-(4-Fluorophenyl)chroman-6-yloxy]pyridin-3-ylamine

Procedure

6-[2-(4-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 3.04 g of 2-[2-(4-fluorophenyl)chroman-6-yloxy]-5-nitropyridine (Example 75(d)). 1H NMR (400 MHz, d6-DMSO) δ: 7.52-7.47 (m, 3H), 7.24 (m, 2H), 7.05 (dd, 1H, J 8.6, 3.0 Hz), 6.84-6.68 (m, 4H), 5.09 (dd, 1H, J 10.2, 2.1 Hz), 5.00 (bs, 2H), 2.93 (m, 1H), 2.69 (m, 1H), 2.13 (m, 1H), 1.98 (m, 1H).

Sources & evidence

ORD record
ord-afa8fb5da54d4e568b06f7be852d209c
Source dataset
uspto-grants-2008_09
Patent number
US07425568B2

Reaction notes

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