5-Bromo-2-nitropyridine → 2-Fluoro-5-(6-nitropyridin-3-yloxy)benzenamine

HRID 1711662Notes

Reaction equation

HRID 1711662 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[CH:6][C:7]=1[F:8].Br[C:11]1[CH:12]=[CH:13][C:14]([N+:17]([O-:19])=[O:18])=[N:15][CH:16]=1>>[F:8][C:7]1[CH:6]=[CH:5][C:4]([O:9][C:11]2[CH:16]=[N:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][CH:12]=2)=[CH:3][C:2]=1[NH2:1]

Participants

3

Reactant 2

HCID 8176205-Bromo-2-nitropyridineHCID 135191803-Amino-4-fluorophenol

Product 1

HCID 672532822-Fluoro-5-(6-nitropyridin-3-yloxy)benzenamineYield 39.3%

Procedure

Using a procedure analogous to Example A3, 3-amino-4-fluorophenol (0.127 g, 1.0 mmol) and 5-bromo-2-nitropyridine (0.203 g, 1.0 mmol) were combined to afford 2-fluoro-5-(6-nitropyridin-3-yloxy)benzenamine (0.098 g, 39% yield) as a yellow solid. 1H NMR (400 MHz, DMSO-d6) δ 8.36 (d, J=2.8 Hz, 1H), 8.30 (d, J=8.8 Hz, 1H), 7.56 (dd, J=8.8, 2.8 Hz, 1H), 7.07 (m, 1H), 6.53 (dd, J=7.6, 3.2 Hz, 1H), 6.31 (s, 1H), 5.48 (s, 2H); MS (ESI) m/z: 250.0 (M+H+).

Sources & evidence

ORD record
ord-115bbfaeb34148b48ceba49967b212fb
Source dataset
uspto-grants-2010_09
Patent number
US07790756B2

Reaction notes

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