Potassium Carbonate → HCID 59596028, compound

HRID 2088999Notes

Reaction equation

HRID 2088999 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[CH:4][N:3]=1.[C:9]1([S:15]([N:18]2[C:22]3=[N:23][CH:24]=[CH:25][CH:26]=[C:21]3[C:20](B3OC(C)(C)C(C)(C)O3)=[CH:19]2)(=[O:17])=[O:16])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C([O-])([O-])=O.[K+].[K+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.COCCOC>[Cl:1][C:2]1[N:7]=[C:6]([C:20]2[C:21]3[C:22](=[N:23][CH:24]=[CH:25][CH:26]=3)[N:18]([S:15]([C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=3)(=[O:17])=[O:16])[CH:19]=2)[CH:5]=[CH:4][N:3]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 775312,4-DichloropyrimidineHCID 455881371-(Phenylsulfonyl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrrolo[2,3-b]pyridine

Product 1

HCID 59596028HCID 59596028, compoundYield 73.8%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
85 °C

Procedure

2,4-dichloropyrimidine (0.192 g, 1.29 mmol), 1-(phenylsulfonyl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine (0.45 g, 1.17 mmol), K2CO3 (1.17 ml, 2.34 mmol), 1,2-dimethoxyethane (5 ml) and tetrakis(triphenylphosphine)palladium (0.054 g, 0.047 mmol) were placed in a 25 mL of flask. The flask was evacuated and purged with nitrogen. The mixture was heated at 85° C. for 20 min then cooled to room temperature. The reaction mixture was filtered to give the title compound (320 mg, 73.7% yield) as white solids.

Workup

  1. customThe flask was evacuated
  2. custompurged with nitrogen
  3. temperaturethen cooled to room temperature
  4. filtrationThe reaction mixture was filtered

Sources & evidence

ORD record
ord-c3e5dac7bd7242699246864fddf45344
Source dataset
uspto-grants-2013_05
Patent number
US08435980B2

Reaction notes

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