Potassium Fluoride → 5-(4-fluoroquinolin-2-yl)-N,N-dimethylpyridin-2-amine

HRID 2361470Notes

Reaction equation

HRID 2361470 reaction equation
[CH3:1][N:2]([CH3:22])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:18]=[C:17]([N+]([O-])=O)[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[N:10]=2)=[CH:5][N:4]=1.[F-:23].[K+]>>[F:23][C:17]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]=[C:9]([C:6]2[CH:7]=[CH:8][C:3]([N:2]([CH3:22])[CH3:1])=[N:4][CH:5]=2)[CH:18]=1

Participants

3

Reactant 2

HCID 522689Potassium FluorideHCID 58362513N,N-dimethyl-5-(4-nitroquinolin-2-yl)pyridin-2-amine

Product 1

HCID 583624625-(4-fluoroquinolin-2-yl)-N,N-dimethylpyridin-2-amineYield 37.4%

Procedure

5-(4-Fluoroquinolin-2-yl)-N,N-dimethylpyridin-2-amine T480 was prepared using general procedure M from N,N-dimethyl-5-(4-nitroquinolin-2-yl)pyridin-2-amine (4 mg, 0.014 mmol) and KF (16 mg, 0.28 mmol). The crude product was purified by silica chromatography to afford 5-(4-fluoroquinolin-2-yl)-N,N-dimethylpyridin-2-amine as a light-brown solid (1.4 mg, 37%). 1H NMR (400 MHz, CDCl3): δ 8.89 (d, J=2.8 Hz, 1H), 8.36 (dd, J=11.6 Hz, 1H), 8.09 (m, 1H), 8.04 (m, 1H), 7.73 (m, 1H), 7.51 (m, 1H), 7.47 (d, J=11.6 Hz, 1H), 6.64 (d, J=9.2 Hz, 1H), 3.19 (s, 6H); MS (ESI): 268 (M+H+).

Workup

  1. custom5-(4-Fluoroquinolin-2-yl)-N,N-dimethylpyridin-2-amine T480 was prepared
  2. customThe crude product was purified by silica chromatography

Sources & evidence

ORD record
ord-d1331a479f9641318beb0fcf4742f5c9
Source dataset
uspto-grants-2014_04
Patent number
US08691187B2

Reaction notes

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