Cesium fluoride → 4-(2-Fluoro-5-methylsulfonylphenyl)-2-methylisoquinolin-1-one

HRID 575664Notes

Reaction equation

[CH3:1][N:2]1[CH:11]=[C:10](B2OC(C)(C)C(C)(C)O2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]1=[O:21].Br[C:23]1[CH:28]=[C:27]([S:29]([CH3:32])(=[O:31])=[O:30])[CH:26]=[CH:25][C:24]=1[F:33].[F-].[Cs+]>COCCOC.CO.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]>[F:33][C:24]1[CH:23]=[CH:28][C:27]([S:29]([CH3:32])(=[O:31])=[O:30])=[CH:26][C:25]=1[C:10]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3](=[O:21])[N:2]([CH3:1])[CH:11]=1

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of compound 2-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)isoquinolin-1-one (4.1 g, 14.5 mmol), 2-bromo-4-methylsulfonyl-1-fluorobenzene (3.5 g, 13.8 mmol) prepared in a similar manner to Example 79 steps 1-2, CsF (6.3 g, 41.3 mmol), and Pd(dppf)Cl2 (1.0 g, 1.38 mmol) in DME (70 mL) and MeOH (35 ml) was stirred at 70° C. for 12 h under N2. The mixture was concentrated and the residue was purified by column chromatography on silica gel (PE:EA=2:1-0:1) to give the title compound (3.4 g, 74.4%) as a red solid. LCMS (M+H)+=331.9 (M+1)+

Workup

concentrationThe mixture was concentrated
customthe residue was purified by column chromatography on silica gel (PE:EA=2:1-0:1)

Sources & evidence

ORD record: ord-5e73275848534ed28973ef408d5e6d1d
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09034900B2

Reaction notes

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