Sodium Carbonate → HCID 89539118, compound

HRID 1498883Notes

Reaction equation

HRID 1498883 reaction equation
Br[C:2]1[C:3]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[C:4]([C:7](=[O:14])[C:8]2[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=2)[S:5][CH:6]=1.[N:20]1[CH:25]=[CH:24][C:23](B(O)O)=[CH:22][CH:21]=1.C([O-])([O-])=O.[Na+].[Na+]>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]>[N:11]1[CH:12]=[CH:13][C:8]([C:7]([C:4]2[S:5][CH:6]=[C:2]([C:23]3[CH:24]=[CH:25][N:20]=[CH:21][CH:22]=3)[C:3]=2[C:15]([O:17][CH2:18][CH3:19])=[O:16])=[O:14])=[CH:9][CH:10]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 2734379(Pyridin-4-yl)boronic acidHCID 89539133HCID 89539133, compound

Product 1

HCID 89539118HCID 89539118, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 218864351,4-Dioxane--water (1/1)Solvent

Conditions

Temperature
100 °C

Procedure

The mixture of ethyl 4-bromo-2-isonicotinoylthiophene-3-carboxylate (325 mg, 0.96 mmol), 4-pyridineboronic acid (177 mg, 1.44 mmol), Na2CO3 (254 mg, 2.4 mmol) and PdCl2(dppf) (63 mg, 0.077 mmol) was dissolved in 12 mL dioxane/H2O (3:1). The mixture was stirred at 100° C. for 2 h. After completion of the reaction the resulting mixture was concentrated under reduced pressure. The material was loaded onto a silica gel column and eluted with 20%-50% EtOAc/PE. Elution fractions containing the desired compounds were collected and the solvent was removed under reduced pressure to provide the title compound (260 mg, 80% yield) as an orange oil. LC-MS (Method A): m/z 339 (M+H)+, Rt: 1.77 min.

Workup

  1. customAfter completion of the reaction the resulting mixture
  2. concentrationwas concentrated under reduced pressure
  3. washeluted with 20%-50% EtOAc/PE
  4. washElution fractions
  5. additioncontaining the desired compounds
  6. customwere collected
  7. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-e215a69e980c4b669a9dacd76fae07cc
Source dataset
uspto-grants-2015_12
Patent number
US09200005B2

Reaction notes

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