Hydrochloric Acid → HCID 118131158, compound

HRID 634372Notes

Reaction equation

Br[C:2]1[C:11]2[C:6](=[CH:7][C:8]([CH3:12])=[CH:9][CH:10]=2)[C:5](=[O:13])[O:4][C:3]=1[CH:14]([OH:16])[CH3:15].[C:17]1(B(O)O)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C([O-])([O-])=O.[Na+].[Na+].Cl>O1CCOCC1.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[OH:16][CH:14]([C:3]1[O:4][C:5](=[O:13])[C:6]2[C:11]([C:2]=1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[CH:10][CH:9]=[C:8]([CH3:12])[CH:7]=2)[CH3:15]

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of 4-bromo-3-(1-hydroxyethyl)-7-methyl-1H-isochromen-1-one (intermediate A4, 1.04 g, 3.67 mmol) in Dioxane/H2O (5:1) (60 ml), phenylboronic acid (0.67 g, 5.51 mmol) and Na2CO3 (0.779 g, 7.34 mmol) were added followed by Pd(dppf)Cl2 (0.269 g, 0.367 mmol) and the resulting mixture was heated at 90° C. for 2 hrs. 1N HCl was added (pH≈2) and the mixture was partitioned between EtOAc and water. The organic phase was washed twice with brine and dried over sodium sulfate. The solvent was removed under vacuum and the crude was purified by flash column chromatography on Biotage silica gel cartridge (cyclohexane:EtOAc=95:5 to 40:60) to afford title compound as a yellow oil (0.835 g, 2.98 mmol, 81%).

Workup

customthe mixture was partitioned between EtOAc and water
washThe organic phase was washed twice with brine
dry with materialdried over sodium sulfate
customThe solvent was removed under vacuum
customthe crude was purified by flash column chromatography on Biotage silica gel cartridge (cyclohexane:EtOAc=95:5 to 40:60)

Sources & evidence

ORD record: ord-fb303f6bcf514f41a701275c8445aaa0
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09321776B2

Reaction notes

Loading…