Cesium carbonate → 4-(3,6-Dihydro-2H-pyran-4-yl)-3-(1-hydroxyethyl)-1H-isochromen-1-one

HRID 634365Notes

Reaction equation

HRID 634365 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].[O:16]1[CH2:21][CH:20]=[C:19](B2OC(C)(C)C(C)(C)O2)[CH2:18][CH2:17]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>[O:16]1[CH2:17][CH:18]=[C:19]([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])[CH2:20][CH2:21]1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 112180533,6-Dihydro-2H-pyran-4-boronic acid pinacol esterHCID 1181312554-Bromo-3-(1-hydroxyethyl)-1H-isochromen-1-one2×

Product 1

HCID 1181310694-(3,6-Dihydro-2H-pyran-4-yl)-3-(1-hydroxyethyl)-1H-isochromen-1-oneYield 26%

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, 0.50 g, 1.86 mmol), 2-(3,6-dihydro-2H-pyran-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (0.51 g, 2.42 mmol), Pd(PPh3)4 (0.11 g, 0.093 mmol) and Cs2CO3 (0.30 mg, 0.93 mmol) to afford the title compound (0.13 g, 26%) as a orange oil.

Sources & evidence

ORD record
ord-d86e868007f9468eb260da383d70d053
Source dataset
uspto-grants-2016_04
Patent number
US09321776B2

Reaction notes

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