5-Chloro-2-methyl-1,8-naphthyridine → (5-Bromo-2-phenoxy-phenyl)-(7-methyl-[1,8]naphthyridin-4-yl)-amine

HRID 2358679Notes

Reaction equation

HRID 2358679 reaction equation
Cl[C:2]1[CH:11]=[CH:10][N:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([CH3:12])=[N:7]2.[Br:13][C:14]1[CH:15]=[CH:16][C:17]([O:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[C:18]([NH2:20])[CH:19]=1>>[Br:13][C:14]1[CH:15]=[CH:16][C:17]([O:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[C:18]([NH:20][C:2]2[C:3]3[C:8](=[N:7][C:6]([CH3:12])=[CH:5][CH:4]=3)[N:9]=[CH:10][CH:11]=2)[CH:19]=1

Participants

3

Reactant 2

HCID 122663725-Chloro-2-methyl-1,8-naphthyridineHCID 161094555-Bromo-2-phenoxyaniline

Product 1

HCID 68461174(5-Bromo-2-phenoxy-phenyl)-(7-methyl-[1,8]naphthyridin-4-yl)-amine

Procedure

The product from Example 1d (278 mg, 1.56 mmol) was reacted with the product from Example 124b (412 mg, 1.56 mmol) for 18 h following the procedure from Example 1g giving the crude title compound which was purified by HPLC with TFA providing the product as a trifluoroacetic acid (206 mg, 25%). 1H NMR (300 MHz, DMSO-d6) δ ppm: 2.73 (s, 3 H) 6.69 (d, J=7.35 Hz, 2 H) 6.96 (d, J=7.72 Hz, 2 H) 7.05-7.15 (m, 3 H) 7.24-7.36 (m, 2 H) 7.68 (dd, J=8.82, 2.57 Hz, 1 H) 7.75 (d, J=8.46 Hz, 1 H) 7.82 (d, J=2.21 Hz, 1 H) 8.52 (d, J=6.99 Hz, 1 H) 8.86 (d, J=8.82 Hz, 1 H) 10.93 (s, 1 H) 14.49 (s, 1 H); MS (ESI+) m/z 408 (M+H−TFA)+.

Sources & evidence

ORD record
ord-04eb0d144e4a47719b937925adba5413
Source dataset
uspto-grants-2010_07
Patent number
US07763731B2

Reaction notes

Loading…