Cesium carbonate → HCID 118131074, compound

HRID 634361Notes

Reaction equation

HRID 634361 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[CH:22]=[C:21](B(O)O)[CH:20]=[CH:19][N: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:21]1[CH:20]=[CH:19][N:18]=[C:17]([CH3:16])[CH:22]=1)=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH3:14]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 41926642-Methylpyridine-4-boronic acidHCID 1181312554-Bromo-3-(1-hydroxyethyl)-1H-isochromen-1-one2×

Product 1

HCID 118131074HCID 118131074, compoundYield 48%

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), 2-methylpyridin-4-ylboronic acid (0.38 g, 2.79 mmol), Pd(PPh3)4 (0.107 g, 0.093 mmol) and Cs2CO3 (0.78 g, 2.41 mmol). The crude was purified via reverse phase chromatography with a Biotage C18 SNAP 30 g column (Phase A, water 95%, ACN 4.9%, formic acid 0.1%; Phase B ACN 99.9%, formic acid 0.1%) to afford the title compound (0.25 g, 48%).

Workup

  1. customThe crude was purified via reverse phase chromatography with a Biotage C18 SNAP 30 g column (Phase A, water 95%, ACN 4.9%, formic acid 0.1%; Phase B ACN 99.9%, formic acid 0.1%)

Sources & evidence

ORD record
ord-288682ba89a144c7b71a3f0b5973ee5f
Source dataset
uspto-grants-2016_04
Patent number
US09321776B2

Reaction notes

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