Bromine → 6-Benzyl-5,6,7,8-tetrahydro-1,6-naphthyridin-2(1H)-one

HRID 1371497Notes

Reaction equation

BrBr.[CH2:3]([N:10]1[CH2:19][CH2:18][C:17]2[NH:16][C:15](=[O:20])[CH2:14][CH2:13][C:12]=2[CH2:11]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>C(O)(=O)C>[CH2:3]([N:10]1[CH2:19][CH2:18][C:17]2[NH:16][C:15](=[O:20])[CH:14]=[CH:13][C:12]=2[CH2:11]1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

Conditions

Temperature: 100 °C

Procedure

Bromine (750 μl, 14.6 mmol) in glacial acetic acid (5 ml) was added dropwise over 5 minutes to (6-benzyl-3,4,5,6,7,8-hexahydro-1H-[1,6]naphthyridin-2-one (3.37 g, 13.9 mmol) (reference WO9830560) dissolved in glacial acetic acid (50 ml) at 100° C. The mixture was heated at 100° C. for 2.5 hours and then was cooled to room temperature. The solvent was evaporated under reduced pressure and the residue was basified with 10% sodium carbonate solution (50 ml). The aqueous mixture was extracted with chloroform (4×50 ml) and the combined organic solutions were dried over sodium sulphate and evaporated under reduced pressure. The residue was purified by chromatography on silica gel using methanol in dichloromethane (gradient from 0:100 to 3:97) to give the title compound as yellow crystals (1.5 g).

Workup

temperaturewas cooled to room temperature
customThe solvent was evaporated under reduced pressure
extractionThe aqueous mixture was extracted with chloroform (4×50 ml)
dry with materialthe combined organic solutions were dried over sodium sulphate
customevaporated under reduced pressure
customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record: ord-f6e528e06a244fa9be9c5f3bba3e3f86
Source dataset: uspto-grants-2007_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07157468B2

Reaction notes

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