Water → HCID 86681454, compound
Reaction equation
[CH3:1][N:2]1[C:6](B2OC(C)(C)C(C)(C)O2)=[CH:5][CH:4]=[N:3]1.Br[C:17]1[CH:18]=[C:19]2[C:23](=[CH:24][CH:25]=1)[C:22](=[O:26])[N:21]([C@@H:27]([CH2:40][C:41]1[CH:46]=[CH:45][CH:44]=[C:43]([F:47])[CH:42]=1)[CH2:28][N:29]1[C:37](=[O:38])[C:36]3[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=3)[C:30]1=[O:39])[CH2:20]2.C(N(CC)C(C)C)(C)C.O1CCOCC1.O>CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C>[CH3:1][N:2]1[C:6]([C:17]2[CH:18]=[C:19]3[C:23](=[CH:24][CH:25]=2)[C:22](=[O:26])[N:21]([C@@H:27]([CH2:40][C:41]2[CH:46]=[CH:45][CH:44]=[C:43]([F:47])[CH:42]=2)[CH2:28][N:29]2[C:37](=[O:38])[C:36]4[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=4)[C:30]2=[O:39])[CH2:20]3)=[CH:5][CH:4]=[N:3]1Participants
7
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 110 °C
Procedure
A mixture of 1-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (0.557 g, 2.68 mmol), bis(tri-t-butylphosphine)palladium (0.114 g, 0.223 mmol), 2-[(2S)-2-(5-bromo-1-oxo-1,3-dihydro-2H-isoindol-2-yl)-3-(3-fluorophenyl)propyl]-1H-isoindole-1,3(2H)-dione (1.10 g, 2.23 mmol) and N,N-diisopropylethylamine (1.16 mL, 6.69 mmol) in 1,4-dioxane (12 mL, 150 mmol) and water (0.60 mL, 33 mmol) was stirred under microwave at 110° C. for 15 minutes. The reaction mixture was filtered through a pad of celite and the filtrate was concentrated under reduced pressure. The residue was purified by combi-flash chromatography eluted with EtOAc/hexane (30-100%) to give 0.72 g (61% yield) of the desired product. LCMS found: 495.1 (M+H)+.
Workup
- filtrationThe reaction mixture was filtered through a pad of celite
- concentrationthe filtrate was concentrated under reduced pressure
- customThe residue was purified by combi-flash chromatography
- washeluted with EtOAc/hexane (30-100%)
Sources & evidence
- ORD record
- ord-48338523239442e09562103fb9abc242
- Source dataset
- uspto-grants-2014_11
- Patent number
- US08895571B2
Reaction notes
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