Cesium carbonate → HCID 58408408, compound

HRID 1948565Notes

Reaction equation

HRID 1948565 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]([C:13]2[CH:18]=[N:17][CH:16]=[CH:15][N:14]=2)=[C:6]([CH:12]=1)[C:7]([O:9][CH2:10][CH3:11])=[O:8].[CH3:19][C:20]1[CH:21]=[C:22](B(O)O)[CH:23]=[N:24][CH:25]=1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH3:19][C:20]1[CH:21]=[C:22]([C:2]2[CH:3]=[CH:4][C:5]([C:13]3[CH:18]=[N:17][CH:16]=[CH:15][N:14]=3)=[C:6]([CH:12]=2)[C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH:23]=[N:24][CH:25]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 27627085-Methylpyridine-3-boronic acidHCID 58408404Ethyl 5-chloro-2-pyrazin-2-ylbenzoate

Product 1

HCID 58408408HCID 58408408, compound

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of ethyl 5-chloro-2-pyrazin-2-ylbenzoate (3-2, 0.120 g, 0.457 mmol, 1.0 equiv), 5-methylpyridine-3-boronic acid (0.094 g, 0.685 mmol, 1.5 equiv), PdCl2(dppf) (0.050 g, 0.069 mmol, 0.1 equiv) and 4M Cs2CO3 (0.400 mL, 1.599 mmol, 3.5 equiv) in DMF (2.3 mL) was combined and heated to 100° C. in a microwave reactor for 2 hours and fifty minutes. The reaction mixture was filtered and put on a reverse phase preparative HPLC system running acetonitrile/water with a TFA buffer (5 to 60% CH3CN in water). The cleanest fractions were pooled, concentrated and freebased to afford the product (3-3) as a white solid. ESI+ MS [M+H]+ C19H17N3O2: 320.1 found, 320.37 required.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-deb7fdaeccfc4f199b4bea94c25625a8
Source dataset
uspto-grants-2013_03
Patent number
US08399494B2

Reaction notes

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