Formic Acid → (+/-)-7-Chloro-1,3,4,10b-tetrahydropyrido[2,1-a]isoindole-2,6-dione

HRID 2287348Notes

Reaction equation

Br[C:2]1[CH:16]=[CH:15][CH:14]=[C:13]([Cl:17])[C:3]=1[C:4]([N:6]1[CH:11]=[CH:10][C:9](=[O:12])[CH2:8][CH2:7]1)=[O:5].C(N(CC)CC)C.C(O)=O>CN(C=O)C>[Cl:17][C:13]1[CH:14]=[CH:15][CH:16]=[C:2]2[C:3]=1[C:4](=[O:5])[N:6]1[CH2:11][CH2:10][C:9](=[O:12])[CH2:8][CH:7]12

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 1-(2-bromo-6-chlorobenzoyl)-2,3-dihydro-4-pyridinone (Preparation 3) (300 mg, 0.954 mmol), triethylamine (0.39 mmol, 0.54 ml), formic acid (0.05 ml, 1.3 mmol) and di(triphenylphosphine)diacetoxypalladium (47 mg, 0.063 mmol) in DMF (3 ml) was heated to 80° C. for 2 h. The cooled solution was filtered through celite, diluted with water, extracted twice with ethyl acetate, the extracts dried over sodium sulphate and evaporated. The residue was purified by flash column chromatography on silica eluting with 50% ethyl acetate in hexane to yield the title compound as a colourless oil (70 mg). MS (+CI) m /z 235/237 [M+H]+.

Workup

filtrationThe cooled solution was filtered through celite
additiondiluted with water
extractionextracted twice with ethyl acetate
dry with materialthe extracts dried over sodium sulphate
customevaporated
customThe residue was purified by flash column chromatography on silica eluting with 50% ethyl acetate in hexane

Sources & evidence

ORD record: ord-cc8251cae7244dcebea2b7876866957d
Source dataset: uspto-grants-2000_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06083952

Reaction notes

Loading…