Dimethyl Sulfoxide → 2-((2,3-dihydrobenzo[1,4]dioxin-6-yl)methyl)-5-iodoisoquinolin-1(2H)-one
Reaction equation
N[C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][N:6]([CH2:13][C:14]1[CH:23]=[CH:22][C:17]3[O:18][CH2:19][CH2:20][O:21][C:16]=3[CH:15]=1)[C:7]2=[O:12].N([O-])=O.[Na+].CS(C)=O.[IH:32].C([O-])(O)=O.[Na+]>>[O:18]1[C:17]2[CH:22]=[CH:23][C:14]([CH2:13][N:6]3[CH:5]=[CH:4][C:3]4[C:8](=[CH:9][CH:10]=[CH:11][C:2]=4[I:32])[C:7]3=[O:12])=[CH:15][C:16]=2[O:21][CH2:20][CH2:19]1Participants
6
Procedure
5-Amino-2-(2,3-dihydro-benzo[1,4]dioxin-6-ylmethyl)-2H-isoquinolin-1-one (260 mg, 0.00084 mol) was added to a solution of sodium nitrite (200 mg, 0.003 mol) in dimethyl sulfoxide (4 mL, 0.06 mol) at 35° C. Aqueous hydrogen iodide (0.5 mL, 0.004 mol) in dimethyl sulfoxide (4 mL, 0.06 mol) was added, and the reaction mixture was stirred for 1 hour. The cooled reaction mixture was neutralized with sat. aq. NaHCO3 and extracted with methylene chloride (3×50 mL). The combined methylene chloride extracts were washed with brine, dried over magnesium sulfate. The solvent was removed in vacuo and the residue was purified via flash column chromatography (12 g of silica gel, 0-50% EtOAc/Hexane) gave a light yellow solid. MS m/z (M+H) 420.0.
Workup
- customThe cooled reaction mixture
- extractionextracted with methylene chloride (3×50 mL)
- washThe combined methylene chloride extracts were washed with brine
- dry with materialdried over magnesium sulfate
- customThe solvent was removed in vacuo
- customthe residue was purified via flash column chromatography (12 g of silica gel, 0-50% EtOAc/Hexane)
- customgave a light yellow solid
Sources & evidence
- ORD record
- ord-344883a6ccfd4c5eb9692ccdb3e6bb68
- Source dataset
- uspto-grants-2014_07
- Patent number
- US08779144B2
Reaction notes
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