Cesium carbonate → HCID 118131268, compound

HRID 634364Notes

Reaction equation

HRID 634364 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][O:17][C:18]1[N:23]=[CH:22][C:21](B(O)O)=[CH:20][CH:19]=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:22]=[N:23][C:18]([O:17][CH3:16])=[CH:19][CH:20]=1)=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH3:14]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 2734368(6-Methoxypyridin-3-yl)boronic acidHCID 1181312554-Bromo-3-(1-hydroxyethyl)-1H-isochromen-1-one2×

Product 1

HCID 118131268HCID 118131268, compoundYield 38%

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, 0.6 g, 2.23 mmol), 6-methoxypyridin-3-ylboronic acid (0.443 g, 2.90 mmol), Pd(PPh3)4 (0.206 g, 0.178 mmol) and Cs2CO3 (1.02 g, 3.1 mmol). The crude was purified via reverse phase chromatography on the Biotage 30 g C18 SNAP column (Phase A, water 95%, acetonitrile 4.9%, formic acid 0.1%; Phase B acetonitrile 99.9%, formic acid 0.1%) to afford the title compound (0.25 g, 38%).

Workup

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

Sources & evidence

ORD record
ord-8c7b32ed83564c8498c38df0816bd29f
Source dataset
uspto-grants-2016_04
Patent number
US09321776B2

Reaction notes

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