Toluene → HCID 86699748, compound
Reaction equation
[CH2:1]([O:3][C:4](=[O:26])[C:5]1[C:10](OS(C(F)(F)F)(=O)=O)=[CH:9][C:8]([N:19]2[CH2:24][CH2:23][O:22][CH2:21][CH2:20]2)=[CH:7][C:6]=1[CH3:25])[CH3:2].[F-].[K+].[Br-].[K+].[CH:31]1(B(O)O)C[CH2:32]1.[C:37]1(C)C=CC=CC=1>>[CH2:1]([O:3][C:4](=[O:26])[C:5]1[C:10]([CH3:37])=[CH:9][C:8]([N:19]2[CH2:24][CH2:23][O:22][CH2:21][CH2:20]2)=[CH:7][C:6]=1[CH:25]1[CH2:32][CH2:31]1)[CH3:2]Participants
Procedure
A solution of 2-methyl-4-morpholin-4-yl-6-(trifluoromethylsulfonyl)oxy-benzoic acid ethyl ester (0.7 g, 1.76 mmol), potassium fluoride (0.43 g, 7.41 mmol), potassium bromide (0.25 g, 2.12 mmol) and cyclopropylboronic acid (0.30 g, 3.53 mmol) in dry toluene (16 ml) is degassed and flushed with argon for 20 min. To the reaction mixture is added tetrakis(triphenylphosphin)palladium(0) (0.20 g, 0.18 mmol) and subjected to microwave irradiation at 120° C. for 1 h. The reaction mixture is poured onto ice and extracted with ethyl acetate (3×30 ml). The combined organic layers are washed with water (20 ml), brine (20 ml) and dried over sodium sulfate. The solvent is evaporated to get the crude product, which is purified by column chromatography (silica gel, 8% acetone/hexane) to afford 2-cyclopropyl-6-methyl-4-morpholin-4-yl-benzoic acid ethyl ester (0.46 g, 1.59 mmol, 85%).
Workup
- customflushed with argon for 20 min
- customirradiation at 120° C. for 1 h
- additionThe reaction mixture is poured onto ice
- extractionextracted with ethyl acetate (3×30 ml)
- washThe combined organic layers are washed with water (20 ml), brine (20 ml)
- dry with materialdried over sodium sulfate
- customThe solvent is evaporated
- customto get the crude product, which
- customis purified by column chromatography (silica gel, 8% acetone/hexane)
Sources & evidence
- ORD record
- ord-652a751bb2b4411b8285909a2daa32f1
- Source dataset
- uspto-grants-2015_08
- Patent number
- US09108936B2
Reaction notes
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