Cesium carbonate → 4-(3-Fluorophenyl)-3-(1-hydroxyethyl)-1H-isochromen-1-one

HRID 634356Notes

Reaction equation

HRID 634356 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].[F:16][C:17]1[CH:18]=[C:19](B(O)O)[CH:20]=[CH:21][CH:22]=1.C([O-])([O-])=O.[Cs+].[Cs+]>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>[F:16][C:17]1[CH:22]=[C:21]([C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5](=[O:12])[O:4][C:3]=2[CH:13]([OH:15])[CH3:14])[CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 27339863-Fluorophenylboronic acidHCID 1181312554-Bromo-3-(1-hydroxyethyl)-1H-isochromen-1-one2×

Product 1

HCID 1181310784-(3-Fluorophenyl)-3-(1-hydroxyethyl)-1H-isochromen-1-oneYield 46.2%

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Procedure

The title compound was made in a similar way as that of the intermediate B1 using 4-bromo-3-(1-hydroxyethyl)-1H-isochromen-1-one (Intermediate A2, 0.8 g, 2.97 mmol), 3-fluorophenylboronic acid (0.62 g, 4.46 mmol), Pd(PPh3)4 (0.17 g, 0.149 mmol) and Cs2CO3 (0.97 g, 2.9 mmol) to afford the title compound (0.39 g, 46%).

Sources & evidence

ORD record
ord-7be990d787c44b33911cd4fd9d899f55
Source dataset
uspto-grants-2016_04
Patent number
US09321776B2

Reaction notes

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