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

HRID 31255Notes

Reaction equation

HRID 31255 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][CH:29]=[CH:28][C:27]=1[CH:32]1[CH2:41][CH2:40][C:39]2[C:34](=[CH:35][CH:36]=[C:37]([O:42][C:43]3[CH:48]=[CH:47][C:46]([N+:49]([O-])=O)=[CH:45][N:44]=3)[CH:38]=2)[O:33]1>>[F:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[CH:32]1[CH2:41][CH2:40][C:39]2[C:34](=[CH:35][CH:36]=[C:37]([O:42][C:43]3[N:44]=[CH:45][C:46]([NH2:49])=[CH:47][CH:48]=3)[CH:38]=2)[O:33]1

Participants

3

Reactant 2

HCID 179784785-Amino-2-(2-phenylchroman-6-yloxy)pyridineHCID 179786462-[2-(2-Fluorophenyl)chroman-6-yloxy]-5-nitropyridine

Product 1

HCID 179785036-[2-(2-Fluorophenyl)chroman-6-yloxy]-pyridin-3-ylamine

Procedure

6-[2-(2-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 240 mg of 2-[2-(2-fluorophenyl)chroman-6-yloxy]-5-nitropyridine (Example 19(d)). 1H NMR (400 MHz, d6-DMSO) δ: 7.52 (m, 1H), 7.51 (d, 1H, J 3.0 Hz), 7.41 (m, 1H), 7.28-7.24 (m, 2H), 7.05 (dd, 1H, J 8.6, 3.0 Hz), 6.81-6.73 (m, 3H), 6.70 (d, 1H, J 8.6 Hz), 5.31 (dd, 1H, J 10.3, 2.2 Hz), 5.00 (s, 2H), 2.98 (m, 1H), 2.72 (m, 1H), 2.15 (m, 1H), 2.06 (m, 1H).

Sources & evidence

ORD record
ord-1c1b91bf6edd4daaa0e6839db28f3959
Source dataset
uspto-grants-2008_09
Patent number
US07425568B2

Reaction notes

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