Cesium carbonate → 3-(1-Hydroxyethyl)-4-phenyl-1H-isochromen-1-one
Reaction equation
Br[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5](=[O:12])[O:4][C:3]=1[CH:13]([OH:15])[CH3:14].[C:16]1(B(O)O)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C.CCOC(C)=O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[OH:15][CH:13]([C:3]1[O:4][C:5](=[O:12])[C:6]2[C:11]([C:2]=1[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH3:14]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 120 °C
Procedure
4-Bromo-3-(1-hydroxyethyl)-1H-isochromen-1-one (Intermediate A2, 0.77 g, 2.88 mmol), phenylboronic acid (0.63 g, 5.18 mmol), Pd(PPh3)4 (0.199 g, 0.173 mmol) and Cs2CO3 (1.49 g, 4.6 mmol) were dissolved in DMF (10.7 ml) and heated under microwave irradiation at 120° C. for 20 min. The reaction mixture was then diluted with AcOEt (100 mL) and filtrate. The organic phase was washed twice with 0.5 M HClaqueous, twice with water, sat NaHCO3 and once with sat NaClaqueous. The resulting organic phase was dried over Na2SO4, filtered and concentrated. The crude was finally purified on Biotage Si 50 g Ultra with a gradient of Hexane and EtOAc. The title compound was recovered as dark pink solid (0.53 g, 1.99 mmol, 69.3%) as a dark pink solid.
Workup
- washThe organic phase was washed twice with 0.5 M HClaqueous, twice with water
- dry with materialThe resulting organic phase was dried over Na2SO4
- filtrationfiltered
- concentrationconcentrated
- customThe crude was finally purified on Biotage Si 50 g Ultra with a gradient of Hexane and EtOAc
Sources & evidence
- ORD record
- ord-5fb022e6d905482a98a2d3bc662e3ad6
- Source dataset
- uspto-grants-2016_04
- Patent number
- US09321776B2
Reaction notes
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