Cesium carbonate → 3-(1-Hydroxyethyl)-4-m-tolyl-1H-isochromen-1-one

HRID 634355Notes

Reaction equation

HRID 634355 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].[C:16]1([CH3:25])[CH:21]=[CH:20][CH:19]=[C:18](B(O)O)[CH: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>[OH:15][CH:13]([C:3]1[O:4][C:5](=[O:12])[C:6]2[C:11]([C:2]=1[C:18]1[CH:17]=[C:16]([CH3:25])[CH:21]=[CH:20][CH:19]=1)=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH3:14]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 27339503-Tolylboronic acidHCID 1181312554-Bromo-3-(1-hydroxyethyl)-1H-isochromen-1-one2×

Product 1

HCID 1181312503-(1-Hydroxyethyl)-4-m-tolyl-1H-isochromen-1-oneYield 55.5%

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, 0.52 g, 1.93 mmol), m-tolylboronic acid (0.45 g, 3.28 mmol), Pd(PPh3)4 (0.11 g, 0.096 mmol) and Cs2CO3 (0.81 g, 2.5 mmol) to afford the title compound (0.3 g, 55%).

Sources & evidence

ORD record
ord-197b5b8874264638a02d0bda94b76d38
Source dataset
uspto-grants-2016_04
Patent number
US09321776B2

Reaction notes

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