2,4-Dichloropyridine → 4-(2-Chloropyridin-4-yloxy)-2-fluorobenzenamine

HRID 2042051Notes

Reaction equation

HRID 2042051 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6](Cl)[CH:5]=[CH:4][N:3]=1.[F:9][C:10]1[CH:11]=[C:12]([OH:17])[CH:13]=[CH:14][C:15]=1[NH2:16]>>[Cl:1][C:2]1[CH:7]=[C:6]([O:17][C:12]2[CH:13]=[CH:14][C:15]([NH2:16])=[C:10]([F:9])[CH:11]=2)[CH:5]=[CH:4][N:3]=1

Participants

3

Reactant 2

HCID 335152,4-DichloropyridineHCID 27359194-Amino-3-fluorophenol

Product 1

HCID 594583014-(2-Chloropyridin-4-yloxy)-2-fluorobenzenamineYield 86%

Procedure

Using a procedure analogous to Example A2, 2,4-dichloropyridine (8.0 g, 54 mmol) and 3-fluoro-4-aminophenol (8.0 g, 62.9 mmol) were combined to provide 4-(2-chloro-pyridin-4-yloxy)-2-fluorophenylamine (11 g, 86% yield). 1H NMR (300 MHz, DMSO-d6) δ 8.24 (d, J=5.7 Hz, 1H), 7.00 (dd, J=9.0, 2.7 Hz, 1H), 6.89-6.73 (m, 4H), 5.21 (br s, 2H); MS (ESI) m/z: 239.2 (M+H+).

Sources & evidence

ORD record
ord-65068ac01c7a4d3eb5b235b20b34efee
Source dataset
uspto-grants-2013_11
Patent number
US08586565B2

Reaction notes

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