Potassium Carbonate → HCID 71557604, compound

HRID 920912Notes

Reaction equation

HRID 920912 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.[F:24][C:25]([F:36])([F:35])[C:26]1[CH:31]=[CH:30][C:29](B(O)O)=[CH:28][CH:27]=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:15]1[C:16]2[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:22]=[CH:23][C:14]=1[CH2:13][CH2:12][N:8]1[C:9](=[O:11])[C:10]2[C:2]([C:29]3[CH:30]=[CH:31][C:26]([C:25]([F:36])([F:35])[F:24])=[CH:27][CH:28]=3)=[CH:3][S:4][C:5]=2[CH:6]=[N:7]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 27343894-(Trifluoromethyl)phenylboronic acidHCID 86683119HCID 86683119, compound

Product 1

HCID 71557604HCID 71557604, compound

Reagents, catalysts & solvents 2

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

Conditions

Temperature
110 °C

Procedure

3-Bromo-5-[2-(quinolin-2-yl)ethyl]thieno[2,3-d]pyridazin-4(5H)-one Example 3.4 (100 mg, 0.26 mmol), 4-(trifluoromethyl)phenylboronic acid (0.26 mmol), Pd(dppf)Cl2 (12.7 mg) and K2CO3 (72 mg, 0.527 mmol) were dissolved in dioxane/H2O (3/1, 2.8 mL). The mixture was stirred at 110° C. for 0.5 h in a microwave tube. The solution was concentrated and purified by prep-TLC to give the title product.

Workup

  1. concentrationThe solution was concentrated
  2. custompurified by prep-TLC

Sources & evidence

ORD record
ord-64ae4852bb174072ace9011a9e2fef7f
Source dataset
uspto-grants-2016_03
Patent number
US09273068B2

Reaction notes

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