Potassium Carbonate → HCID 86683124, compound

HRID 920913Notes

Reaction equation

HRID 920913 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]=[C:19]([F:24])[CH:20]=4)[N:15]=3)[N:7]=[CH:6][C:5]=2[S:4][CH:3]=1.[N:25]1[CH:30]=[CH:29][C:28](B(O)O)=[CH:27][CH:26]=1.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.O.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]>[F:24][C:19]1[CH:20]=[C:21]2[C:16](=[CH:17][CH:18]=1)[N:15]=[C:14]([CH2:13][CH2:12][N:8]1[C:9](=[O:11])[C:10]3[C:2]([C:28]4[CH:29]=[CH:30][N:25]=[CH:26][CH:27]=4)=[CH:3][S:4][C:5]=3[CH:6]=[N:7]1)[CH:23]=[CH:22]2

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 2734379(Pyridin-4-yl)boronic acidHCID 86683125HCID 86683125, compound

Product 1

HCID 86683124HCID 86683124, compoundYield 68.6%

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

3-Bromo-5-(2-(6-fluoroquinolin-2-yl)ethyl)thieno[2,3-d]pyridazin-4(5H)-one (66 mg, 0.163 mmol) was dissolved in dioxane (2.1 mL) and H2O (0.7 mL), pyridin-4-yl boronic acid (20.07 mg, 0.163 mmol), K2CO3 (45.1 mg, 0.327 mmol) and Pd(dppf)Cl2 (7.23 mg, 9.80 μmol) were each added sequentially to the suspension. The suspension was heated in a microwave tube at about 110° C. for 1 h. The crude product was purified by TLC (EA) to give the title compound (45 mg, yield: 68.5%).

Workup

  1. additioneach added sequentially to the suspension
  2. customThe crude product was purified by TLC (EA)

Sources & evidence

ORD record
ord-b8279ae550984501938c04b51ad718e8
Source dataset
uspto-grants-2016_03
Patent number
US09273068B2

Reaction notes

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