Sodium Carbonate → HCID 86683126, compound

HRID 920914Notes

Reaction equation

HRID 920914 reaction equation
Br[C:2]1[C:10]2[C:9](=[O:11])[N:8]([CH2:12][C:13]([F:25])([F:24])[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:26]1[CH:31]=[CH:30][C:29](B(O)O)=[CH:28][CH:27]=1.C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.O.C(Cl)Cl.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].C(Cl)Cl>[F:24][C:13]([F:25])([C:14]1[CH:23]=[CH:22][C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[N:15]=1)[CH2:12][N:8]1[C:9](=[O:11])[C:10]2[C:2]([C:29]3[CH:30]=[CH:31][N:26]=[CH:27][CH:28]=3)=[CH:3][S:4][C:5]=2[CH:6]=[N:7]1

Participants

8

Reactant 3

HCID 10340Sodium CarbonateHCID 2734379(Pyridin-4-yl)boronic acidHCID 86683127HCID 86683127, compound

Product 1

HCID 86683126HCID 86683126, compoundYield 80.6%

Reagents, catalysts & solvents 4

HCID 178418807HCID 178418807, compoundCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 3-bromo-5-(2,2-difluoro-2-(quinolin-2-yl)ethyl)thieno[2,3-d]pyridazin-4(5H)-one (0.118 mmol), pyridin-4-yl boronic acid (0.118 mmol), Na2CO3 (31.4 mg, 0.296 mmol) and PdCl2(dppf)-CH2Cl2 adduct (9.67 mg, 0.012 mmol) in dioxane (1.5 mL) and water (0.5 mL) was stirred at 100° C. for 2 h. The solvent was evaporated and the residue was purified by Pre-TLC (PE/EA=1/1) to give a crude yellow solid. The solid was dissolved in DCM (1.5 mL) and filtered. The white solid obtained was the title compound (40 mg, yield 80%).

Workup

  1. customThe solvent was evaporated
  2. customthe residue was purified by Pre-TLC (PE/EA=1/1)
  3. customto give a crude yellow solid
  4. filtrationfiltered
  5. customThe white solid obtained

Sources & evidence

ORD record
ord-c86daa47f9924040946a8b5e1ae46e36
Source dataset
uspto-grants-2016_03
Patent number
US09273068B2

Reaction notes

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