Cesium carbonate → 3-(1-Hydroxyethyl)-4-(6-methylpyridin-3-yl)-1H-isochromen-1-one

HRID 634358Notes

Reaction equation

HRID 634358 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][C:17]1[N:22]=[CH:21][C:20](B(O)O)=[CH:19][CH:18]=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:20]1[CH:21]=[N:22][C:17]([CH3:16])=[CH:18][CH:19]=1)=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH3:14]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 27630812-Methylpyridine-5-boronic acidHCID 1181312554-Bromo-3-(1-hydroxyethyl)-1H-isochromen-1-one2×

Product 1

HCID 1181311083-(1-Hydroxyethyl)-4-(6-methylpyridin-3-yl)-1H-isochromen-1-oneYield 29%

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, 0.55 g, 2.04 mmol), 6-methylpyridin-3-ylboronic acid (0.550 g, 2.0 mmol), Pd(PPh3)4 (0.118 g, 0.102 mmol) and Cs2CO3 (1.06 g, 3.27 mmol) to afford the title compound (0.163 g, 28%)

Sources & evidence

ORD record
ord-a687e421b1de4a43a025f66b39006fe0
Source dataset
uspto-grants-2016_04
Patent number
US09321776B2

Reaction notes

Loading…