Triethylamine → HCID 22934669, compound
Reaction equation
Br[C:2]1[CH:9]=[CH:8][C:7]([F:10])=[CH:6][C:3]=1[CH:4]=O.C(N(CC)CC)C.C([NH:21][C:22](=[CH2:27])[C:23]([O:25][CH3:26])=[O:24])(=O)C.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CN(C)C=O>[F:10][C:7]1[CH:6]=[C:3]2[C:2]([CH:27]=[C:22]([C:23]([O:25][CH3:26])=[O:24])[N:21]=[CH:4]2)=[CH:9][CH:8]=1Participants
Conditions
- Temperature
- 110 °C
Procedure
A sealed tube was charged with 2-bromo-5-fluorobenzaldehyde (300 mg, 1.47 mmol), dry dimethylformamide (1.5 ml), triethylamine (0.7 ml, 5.02 mmol), methyl 2-acetamidoacrylate (273 mg, 1.91 mmol), tris-o-tolyl-phosphine (89 mg, 0.29 mmol) and palladium acetate (33 mg, 0.14 mmol). The solution was degassed with Argon for 10 min. and then warmed at 110° C. for 4.5 hours. The mixture was cooled to room temperature and poured onto an aqueous solution of ammonium chloride. The mixture was extracted with ethyl acetate, washed with brine, dried over sodium sulfate and concentrated. The residue was purified by flash chromatography over silica gel (gradient cyclohexane/dichloromethane: 0-80%) to yield methyl 7-fluoro-isoquinoline-3-carboxylate (120 mg, 39%) as beige solid.
Workup
- customThe solution was degassed with Argon for 10 min.
- temperatureThe mixture was cooled to room temperature
- additionpoured onto an aqueous solution of ammonium chloride
- extractionThe mixture was extracted with ethyl acetate
- washwashed with brine
- dry with materialdried over sodium sulfate
- concentrationconcentrated
- customThe residue was purified by flash chromatography over silica gel (gradient cyclohexane/dichloromethane: 0-80%)
Sources & evidence
- ORD record
- ord-fcbec923f2cf449a81004a78447d24eb
- Source dataset
- uspto-grants-2015_02
- Patent number
- US08962627B2
Reaction notes
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