6-Chloro-4-phenylamino-pyridine-3-carbaldehyde → 3-(3-amino-4-fluorophenyl)-7-chloro-1-phenyl-1,6-naphthyridin-2(1H)-one

HRID 1930300Notes

Reaction equation

HRID 1930300 reaction equation
[Cl:1][C:2]1[CH:9]=[C:8]([NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:5]([CH:6]=O)=[CH:4][N:3]=1.[NH2:17][C:18]1[CH:19]=[C:20]([CH2:25][C:26](OCC)=[O:27])[CH:21]=[CH:22][C:23]=1[F:24]>CC(N(C)C)=O>[NH2:17][C:18]1[CH:19]=[C:20]([C:25]2[C:26](=[O:27])[N:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:8]3[C:5]([CH:6]=2)=[CH:4][N:3]=[C:2]([Cl:1])[CH:9]=3)[CH:21]=[CH:22][C:23]=1[F:24]

Participants

4

Reactant 2

HCID 592123486-Chloro-4-phenylamino-pyridine-3-carbaldehydeHCID 68983893Ethyl 2-(3-amino-4-fluorophenyl)acetate

Product 1

HCID 866201603-(3-amino-4-fluorophenyl)-7-chloro-1-phenyl-1,6-naphthyridin-2(1H)-oneYield 55%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

A mixture of 6-Chloro-4-(phenylamino)nicotinaldehyde (3 g, 13 mmol), ethyl 2-(3-amino-4-fluorophenyl)acetate (2.6 g, 13 mmol), and KF/Al2O3 (40 wt %, 10 g, 69 mmol) in DMAc (30 mL) was stirred at RT for 2 hours. The solids were removed by filtration and the filtrate was concentrated in vacuo. Recrystallization (EtOAc) provided 3-(3-amino-4-fluorophenyl)-7-chloro-1-phenyl-1,6-naphthyridin-2(1H)-one (2.6 g, 55% yield). 1H NMR (400 MHz, DMSO-d6): δ 8.81 (s, 1 H), 8.20 (s, 1 H), 7.62-7.56 (m, 3 H), 7.40 (d, J=7.2 Hz, 2 H), 7.13 (d, J=7.6 Hz, 1 H), 7.02 (t, J=10.0 Hz, 1 H), 6.82 (m, 1 H), 6.26 (s, 1 H), 5.19 (s, 2 H); MS (ESI) m/z: 366.2 [M+H]+.

Workup

  1. customThe solids were removed by filtration
  2. concentrationthe filtrate was concentrated in vacuo
  3. customRecrystallization (EtOAc)

Sources & evidence

ORD record
ord-5b3a99283df34e96869bb36732b21979
Source dataset
uspto-grants-2012_05
Patent number
US08188113B2

Reaction notes

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