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

HRID 634352Notes

Reaction equation

HRID 634352 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[CH2:13][OH:14].[F:15][C:16]1[CH:17]=[C:18](B(O)O)[CH:19]=[CH:20][CH:21]=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:15][C:16]1[CH:21]=[C:20]([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[CH2:13][OH:14])[CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 27339863-Fluorophenylboronic acidHCID 160500224-bromo-3-(hydroxymethyl)-1H-isochromen-1-one2×

Product 1

HCID 1181311434-(3-Fluorophenyl)-3-(hydroxymethyl)-1H-isochromen-1-oneYield 40%

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Procedure

The title compound was made in a similar way as that of the intermediate B2 using 4-bromo-3-(hydroxymethyl)-1H-isochromen-1-one (Intermediate A1, 0.5 g, 1.960 mmol), 3-fluorophenylboronic acid (0.4 g, 2.86 mmol), Pd(PPh3)4 (0.136 g, 0.118 mmol) and Cs2CO3 (0.96 g, 2.94 mmol) to afford the title compound (0.21 g, 40%).

Sources & evidence

ORD record
ord-aa49ca1ba8dd4215bf0a5d328e735bc0
Source dataset
uspto-grants-2016_04
Patent number
US09321776B2

Reaction notes

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