3-Fluoroaniline → 6-Fluoro-4-(3-fluorophenylamino)-1,7-naphthyridine-3-carbonitrile

HRID 2113564Notes

Reaction equation

Cl[C:2]1[C:11]2[C:6](=[CH:7][N:8]=[C:9]([F:12])[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:13]#[N:14].[F:15][C:16]1[CH:17]=[C:18]([CH:20]=[CH:21][CH:22]=1)[NH2:19]>>[F:12][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][N:8]=1)[N:5]=[CH:4][C:3]([C:13]#[N:14])=[C:2]2[NH:19][C:18]1[CH:20]=[CH:21][CH:22]=[C:16]([F:15])[CH:17]=1

Participants

Reactant 2

HCID 97423-Fluoroaniline

HCID 185489604-Chloro-6-fluoro-1,7-naphthyridine-3-carbonitrile

Product 1

HCID 693209656-Fluoro-4-(3-fluorophenylamino)-1,7-naphthyridine-3-carbonitrileYield 45.2%

Procedure

Following the procedure described above in Example 13, 4-chloro-6-fluoro-1,7-naphthyridine-3-carbonitrile (0.300 g, 1.45 mmol) was reacted with 3-fluoroaniline (0.15 mL, 0.18 g, 1.6 mmol). The crude product was purified by flash chromatography over silica gel (10% EtOAc in CH2Cl2) to give pure 6-fluoro-4-(3-fluorophenylamino)-1,7-naphthyridine-3-carbonitrile (0.185 g, 45% yield): 1H NMR (400 MHz, DMSO-D6) δ 7.16 (td, J=8.5, 2.7 Hz, 1 H) 7.22 (ddd, J8.0, 2.0, 0.9 Hz, 1 H) 7.27 (dt, J=10.2, 2.2 Hz, 1 H) 7.43-7.53 (m, 1 H) 8.17 (s, 1 H) 8.72 (s, 1 H) 9.10 (s, 1 H) 10.16 (s, 1 H).

Workup

customThe crude product was purified by flash chromatography over silica gel (10% EtOAc in CH2Cl2)

Sources & evidence

ORD record: ord-540bfee556094baa860eaf96da366ef8
Source dataset: uspto-grants-2008_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07432279B2

Reaction notes

Loading…