Methyl Acrylate → 3-[4-Fluoro-2-(morpholine-4-sulfonyl)-phenyl]-acrylic acid methyl ester
Reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5](OS(C(F)(F)F)(=O)=O)=[C:4]([S:16]([N:19]2[CH2:24][CH2:23][O:22][CH2:21][CH2:20]2)(=[O:18])=[O:17])[CH:3]=1.[C:25]([O:29][CH3:30])(=[O:28])[CH:26]=[CH2:27].C1C=CC(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCN(C(C)C)C(C)C>CN(C=O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:30][O:29][C:25](=[O:28])[CH:26]=[CH:27][C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][C:4]=1[S:16]([N:19]1[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1)(=[O:18])=[O:17]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 120 °C
Procedure
To a solution of the product of example 85 (100 mg 0.254 mmol) in dry DMF (3 ml) was added methyl acrylate (0.09 ml, 1.02 mmol), Pd(PPh3)2Cl2(17.83 mg, 0.0254 mmol), DPPP (10.5 mg, 0.0254 mmol) and DIPEA (0.2 ml, 1.02 mmol) successively at room temperature in sealed tube. The mixture was heated at 120° C. for about 24 h. After cooling to room temperature, the mixture was poured into ice water and extracted with EA three times. The combined extracts were washed with brine, dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography (PE/EA=5/1) to give the desire product (36 mg, yield 43%).
Workup
- temperatureAfter cooling to room temperature
- extractionextracted with EA three times
- washThe combined extracts were washed with brine
- dry with materialdried over sodium sulfate
- concentrationconcentrated under reduced pressure
- customThe residue was purified by column chromatography (PE/EA=5/1)
Sources & evidence
- ORD record
- ord-4c9b6dc3ad844a099ff4132fb7c3c6bf
- Source dataset
- uspto-grants-2013_04
- Patent number
- US08431581B2
Reaction notes
Loading…