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

HRID 634357Notes

Reaction equation

HRID 634357 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].[CH3:16][N:17]([CH3:27])[C:18]1[CH:19]=[C:20](B(O)O)[CH:21]=[CH:22][CH:23]=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>[CH3:16][N:17]([CH3:27])[C:18]1[CH:23]=[C:22]([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:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 27625273-(Dimethylamino)benzeneboronic acidHCID 1181312554-Bromo-3-(1-hydroxyethyl)-1H-isochromen-1-one2×

Product 1

HCID 1181312514-(3-(Dimethylamino)phenyl)-3-(1-hydroxyethyl)-1H-isochromen-1-oneYield 35%

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, 0.5 g, 1.86 mmol), 3-(dimethylamino)phenylboronic acid (0.46 g, 2.79 mmol), Pd(PPh3)4 (0.11 g, 0.093 mmol) and Cs2CO3 (0.78 g, 2.41 mmol) to afford the title compound (0.2 g, 35%).

Sources & evidence

ORD record
ord-e490a6455fdf4712a12fdd5a455a0f95
Source dataset
uspto-grants-2016_04
Patent number
US09321776B2

Reaction notes

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