Potassium Carbonate → 4-(5-methyl-1-tosyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-2-(methylthio)pyrimidine-5-carbonitrile

HRID 40871Notes

Reaction equation

HRID 40871 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[C:10](B3OC(C)(C)C(C)(C)O3)=[CH:9][N:8]([S:20]([C:23]3[CH:29]=[CH:28][C:26]([CH3:27])=[CH:25][CH:24]=3)(=[O:22])=[O:21])[C:5]2=[N:6][CH:7]=1.Cl[C:31]1[C:36]([C:37]#[N:38])=[CH:35][N:34]=[C:33]([S:39][CH3:40])[N:32]=1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C>[CH3:1][C:2]1[CH:3]=[C:4]2[C:10]([C:31]3[C:36]([C:37]#[N:38])=[CH:35][N:34]=[C:33]([S:39][CH3:40])[N:32]=3)=[CH:9][N:8]([S:20]([C:23]3[CH:29]=[CH:28][C:26]([CH3:27])=[CH:25][CH:24]=3)(=[O:22])=[O:21])[C:5]2=[N:6][CH:7]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 131141834-Chloro-2-(methylsulfanyl)pyrimidine-5-carbonitrileHCID 577743345-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 594144754-(5-methyl-1-tosyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-2-(methylthio)pyrimidine-5-carbonitrileYield 87.5%

Reagents, catalysts & solvents 2

HCID 178418851HCID 178418851, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 5-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine (306 mg, 0.74 mmol) and 4-chloro-2-(methylthio)pyrimidine-5-carbonitrile (207 mg, 1.12 mmol) in dioxane (9 mL) was degassed and stirred under nitrogen for 10 minutes. The reaction mixture was treated with potassium carbonate (336 mg, 2.23 mmol) and bis(tri-t-butylphosphine)palladium(0) (38 mg, 0.074 mmol) and degassed again. The reaction mixture and stirred under nitrogen for 10 minutes. Water (1.35 mL) was added and the reaction mixture was degassed and stirred under nitrogen for 2 hours. A suspension was observed. The resulting mixture was filtered and the solid was washed with dioxane and water. The solid was dried in a vacuum oven to afford the title compound as a white solid (282 mg, 87% yield).

Workup

  1. customwas degassed
  2. customdegassed again
  3. stirringThe reaction mixture and stirred under nitrogen for 10 minutes
  4. additionWater (1.35 mL) was added
  5. customthe reaction mixture was degassed
  6. stirringstirred under nitrogen for 2 hours
  7. filtrationThe resulting mixture was filtered
  8. washthe solid was washed with dioxane and water
  9. customThe solid was dried in a vacuum oven

Sources & evidence

ORD record
ord-5a3ed150828343f99edfb7e00e54513b
Source dataset
uspto-grants-2013_09
Patent number
US08530489B2

Reaction notes

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