Potassium Carbonate → HCID 71557602, compound

HRID 920907Notes

Reaction equation

HRID 920907 reaction equation
Br[C:2]1[C:10]2[C:9](=[O:11])[N:8]([CH2:12][CH2:13][C:14]3[CH:23]=[CH:22][C:21]4[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=4)[N:15]=3)[N:7]=[CH:6][C:5]=2[S:4][CH:3]=1.[N:24]1[CH:29]=[CH:28][C:27](B(O)O)=[CH:26][CH:25]=1.C([O-])([O-])=O.[K+].[K+]>CC(=O)OCC.CCCCCCC.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]>[N:24]1[CH:29]=[CH:28][C:27]([C:2]2[C:10]3[C:9](=[O:11])[N:8]([CH2:12][CH2:13][C:14]4[CH:23]=[CH:22][C:21]5[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=5)[N:15]=4)[N:7]=[CH:6][C:5]=3[S:4][CH:3]=2)=[CH:26][CH:25]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 2734379(Pyridin-4-yl)boronic acidHCID 86683119HCID 86683119, compound

Product 1

HCID 71557602HCID 71557602, compoundYield 70.9%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 21899848Ethylacetate heptaneSolvent

Conditions

Temperature
120 °C

Procedure

3-Bromo-5-[2-(quinolin-2-yl)ethyl]thieno[2,3-d]pyridazin-4(5H)-one (130 mg, 0.33 mmol), pyridine-4-ylboronic acid (45.7 mg, 0.37 mmol), Pd(dppf)Cl2 (15 mg) and K2CO3 (93 mg, 0.67 mmol) were dissolved in dioxane/H2O (3/1, 2.8 mL). The mixture was stirred in nitrogen atmosphere at 120° C. for 1 h in a microwave tube. The solution was concentrated and purified by TLC (DCM/MeOH=10/1) and recrystallized from MeOH to give the title product (90 mg, 69.4%).

Workup

  1. concentrationThe solution was concentrated
  2. custompurified by TLC (DCM/MeOH=10/1)
  3. customrecrystallized from MeOH

Sources & evidence

ORD record
ord-46a6a7d5bb934c50a162864c88cd9be9
Source dataset
uspto-grants-2016_03
Patent number
US09273068B2

Reaction notes

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