Dimethylformamide → 5-Bromo-8-(2-chlorobenzylthio)-6-ethoxy-1,7-naphthyridine

HRID 1881764Notes

Reaction equation

[Br:1][C:2]1[C:11]([O:12][CH2:13][CH3:14])=[N:10][C:9](F)=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.C([O-])([O-])=O.[K+].[K+].CN(C=O)C.[Cl:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[CH2:34][SH:35]>O>[Br:1][C:2]1[C:11]([O:12][CH2:13][CH3:14])=[N:10][C:9]([S:35][CH2:34][C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=2[Cl:27])=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2

Participants

Conditions

Temperature: 100 °C

Procedure

To a 5 mL microwave reactor vial was added 5-bromo-6-ethoxy-8-fluoro-1,7-naphthyridine (100 mg, 0.37 mmol), a large excess of K2CO3, followed by DMF (5 mL). (2-chlorophenyl)methanethiol (70 mg, 0.44 mmol) was then added to the mixture, the vessel was capped and heated under microwave irradiation for 20 min at 100° C. The reaction was diluted with water and extracted with ethyl acetate. The organic layer was washed with brine, dried over Na2SO4 and concentrated. The resultant residue was purified by silica gel to yield 5-bromo-8-(2-chlorobenzylthio)-6-ethoxy-1,7-naphthyridine as a pale yellow solid (100 mg, 0.24 mmol, 66%). 1H NMR (400 MHz, CDCl3): δ ppm 8.74 (d, J=2.64 Hz, 1H), 8.34 (d, J=7.47 Hz, 1H), 7.50-7.68 (m, 2H), 7.35-7.48 (m, 1H), 7.11-7.22 (m, 2H), 4.67 (s, 2H), 4.53 (q, J=7.03 Hz, 2H), 1.41 (t, J=7.03 Hz, 3H). LC/MS m/z 411 [M+H].

Workup

customthe vessel was capped
extractionextracted with ethyl acetate
washThe organic layer was washed with brine
dry with materialdried over Na2SO4
concentrationconcentrated
customThe resultant residue was purified by silica gel

Sources & evidence

ORD record: ord-ff44b610898e4e49b7c9b51b6fd00f85
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08318941B2

Reaction notes

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