Sodium Carbonate → HCID 58203484, compound

HRID 2194787Notes

Reaction equation

HRID 2194787 reaction equation
[CH:1]([C:4]1[C:5](OS(C(F)(F)F)(=O)=O)=[N:6][C:7]([O:12][CH3:13])=[N:8][C:9]=1[O:10][CH3:11])([CH3:3])[CH3:2].[N:22]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH:25]=[C:24](B(O)O)[CH:23]=1.C([O-])([O-])=O.[Na+].[Na+]>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].COCCOC>[CH:1]([C:4]1[C:5]([C:24]2[CH:23]=[N:22][C:31]3[C:26]([CH:25]=2)=[CH:27][CH:28]=[CH:29][CH:30]=3)=[N:6][C:7]([O:12][CH3:13])=[N:8][C:9]=1[O:10][CH3:11])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 2734663Quinoline-3-boronic acidHCID 58203520HCID 58203520, compound

Product 1

HCID 58203484HCID 58203484, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
130 °C

Procedure

In a 5 mL microwave reaction tube, trifluoro-methanesulfonic acid 5-isopropyl-2,6-dimethoxy-pyrimidin-4-yl ester (30 mg, 0.091 mmol), 3-quinoline boronic acid (19 mg, 1.2 eq.) and Pd(dppf)2Cl2 (7.4 mg, 10%) were mixed with 2 mL DME and 0.18 mL 2M aqueous Na2CO3 (4 eq.). The reaction mixture was heated in microwave at 130° C. for 40 minutes. The reaction mixture was concentrated down and purified by reverse phase prep HPLC (MeCN/water) to give a white powder (14 mg, 50%). LC-MS shows 310.2 (M+1).

Workup

  1. concentrationThe reaction mixture was concentrated down
  2. custompurified by reverse phase prep HPLC (MeCN/water)

Sources & evidence

ORD record
ord-a6b72d0fb68f4c1baf28756753b934d9
Source dataset
uspto-grants-2012_12
Patent number
US08334295B2

Reaction notes

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