Cesium carbonate → HCID 86683132, compound

HRID 920918Notes

Reaction equation

HRID 920918 reaction equation
Br[C:2]1[C:10]2[C:9](=[O:11])[N:8]([CH2:12][CH2:13][C:14]3[N:15]=[C:16]4[CH:21]=[C:20]([F:22])[CH:19]=[CH:18][N:17]4[CH:23]=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.[Cs+].[Cs+]>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].C(Cl)Cl>[F:22][C:20]1[CH:19]=[CH:18][N:17]2[CH:23]=[C:14]([CH2:13][CH2:12][N:8]3[C:9](=[O:11])[C:10]4[C:2]([C:27]5[CH:28]=[CH:29][N:24]=[CH:25][CH:26]=5)=[CH:3][S:4][C:5]=4[CH:6]=[N:7]3)[N:15]=[C:16]2[CH:21]=1

Participants

7

Reactant 3

HCID 10796Cesium carbonateHCID 2734379(Pyridin-4-yl)boronic acidHCID 86683130HCID 86683130, compound

Product 1

HCID 86683132HCID 86683132, compound

Reagents, catalysts & solvents 3

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

Conditions

Temperature
110 °C

Procedure

A mixture of 3-bromo-5-(2-(7-fluoroimidazo[1,2-a]pyridin-2-yl)ethyl)thieno[2,3-d]pyridazin-4(5H)-one (80 mg, 0.203 mmol), pyridin-4-ylboronic acid (37.5 mg, 0.305 mmol), PdCl2(dppf)-CH2Cl2 adduct (16.61 mg, 0.020 mmol) and Cs2CO3 (133 mg, 0.407 mmol) in 1,4-dioxane (3 mL) and water(1.5 mL) was heated under microwave at about 110° C. for about 15 min. The mixture was concentrated and was chromatographed on the ISCO Combiflash system using a 40 g Silicycle SiliaSep Silica gel column C-18 column using the following gradient: A: Water (0.1% NH4HCO3); B: Methanol; 30% B to 80% B over 20 min (15 mg, 18.8%).

Workup

  1. concentrationThe mixture was concentrated
  2. customwas chromatographed on the ISCO Combiflash system

Sources & evidence

ORD record
ord-232937502677437286f8c86497da109a
Source dataset
uspto-grants-2016_03
Patent number
US09273068B2

Reaction notes

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