Acetone → 7-Iodo-1,1-dimethyl-1,2,3,4-tetrahydro-benzo[4,5]furo[2,3-c]pyridine
Reaction equation
[I:1][C:2]1[CH:13]=[CH:12][C:5]2[C:6]([CH2:9][CH2:10][NH2:11])=[CH:7][O:8][C:4]=2[CH:3]=1.CO.[CH3:16][C:17]([CH3:19])=O>>[I:1][C:2]1[CH:13]=[CH:12][C:5]2[C:6]3[CH2:9][CH2:10][NH:11][C:17]([CH3:19])([CH3:16])[C:7]=3[O:8][C:4]=2[CH:3]=1Participants
Procedure
To a solution of 2-(6-iodo-benzofuran-3-yl)-ethylamine (4.20 g, 14.63 mmol) in methanol (60.0 mL, 1.48 mol) was added acetone (1.63 mL) and the reaction mixture was stirred at rt. After 2 days the solvent was evaporated. The residue was dissolved in a mixture of TFA (7.0 mL) and DCE (70.0 mL) and heated to reflux. After 20 h the reaction mixture was cooled down and basified with 5M aq. NaOH. The layers were separated and the aqueous phase extracted with DCM. The combined organic layers was dried (Na2SO4) and the solvent was evaporated. The residue was purified on a silica gel column eluting with DCM-MeOH—NH4OH to afford 7-iodo-1,1-dimethyl-1,2,3,4-tetrahydro-benzo[4,5]furo[2,3-c]pyridine as an off-white solid. mp 97-98° C.; MS m/z 328 [M+H]+.
Workup
- customAfter 2 days the solvent was evaporated
- dissolutionThe residue was dissolved in a mixture of TFA (7.0 mL) and DCE (70.0 mL)
- temperatureheated to reflux
- temperatureAfter 20 h the reaction mixture was cooled down
- customThe layers were separated
- extractionthe aqueous phase extracted with DCM
- dry with materialThe combined organic layers was dried (Na2SO4)
- customthe solvent was evaporated
- customThe residue was purified on a silica gel column
- washeluting with DCM-MeOH—NH4OH
Sources & evidence
- ORD record
- ord-acad01631e46431390fca8170d3c8dad
- Source dataset
- uspto-grants-2014_07
- Patent number
- US08765779B2
Reaction notes
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