18-Crown-6 → 3-Fluorobenzo[f][1,7]naphthyridin-5-amine

HRID 340214Notes

Reaction equation

HRID 340214 reaction equation
Cl[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[C:5]([NH2:16])[N:6]=[C:7]3[CH:15]=[CH:14][CH:13]=[CH:12][C:8]3=2)[N:3]=1.[F-:17].[K+].C1OCCOCCOCCOCCOCCOC1>CN1CCCC1=O>[F:17][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[C:5]([NH2:16])[N:6]=[C:7]3[CH:15]=[CH:14][CH:13]=[CH:12][C:8]3=2)[N:3]=1

Participants

5

Reactant 3

HCID 2855718-Crown-6HCID 522689Potassium FluorideHCID 582136303-Chlorobenzo[f][1,7]naphthyridin-5-amine

Product 1

HCID 442306263-Fluorobenzo[f][1,7]naphthyridin-5-amine

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A solution of 3-chlorobenzo[f][1,7]naphthyridin-5-amine (Example 20) (1.0 eq.), potassium fluoride (3.0 eq.), and 18-crown-6 (0.2 eq.) in N-methylpyrrolidone (NMP) (0.4 M) was heated in a microwave reactor at 210° C. for 80 minutes. After cooling to room temperature, the crude reaction mixture was purified by HPLC using 10-50% acetonitrile in water to give 3-fluorobenzo[f][1,7]naphthyridin-5-amine. 1H NMR (acetone d-6): δ 11.40 (br, 2H), 9.38-9.42 (dd, 1H), 8.60 (d, 1H), 7.89-7.92 (dd, 1H), 7.81-7.83 (m, 2H), 7.59-7.66 (m, 1H). LRMS [M+H]=214.1

Workup

  1. customthe crude reaction mixture
  2. customwas purified by HPLC

Sources & evidence

ORD record
ord-dbbbd79acf564f42a41fd7f2a0ef108c
Source dataset
uspto-grants-2014_11
Patent number
US08895577B2

Reaction notes

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