2-(Tributylstannyl)pyridine → HCID 16071782, compound

HRID 1710703Notes

Reaction equation

HRID 1710703 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]([CH:11]2[CH2:13][CH2:12]2)=[O:10])[CH:5]=[N:4][C:3]=1[C:14]1[CH:19]=[CH:18][N:17]=[CH:16][C:15]=1[Cl:20].C([Sn](CCCC)(CCCC)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=1)CCC>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.C1(C)C(C)=CC=CC=1>[Cl:20][C:15]1[CH:16]=[N:17][CH:18]=[CH:19][C:14]=1[C:3]1[N:4]=[CH:5][C:6]([NH:8][C:9]([CH:11]2[CH2:13][CH2:12]2)=[O:10])=[N:7][C:2]=1[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=1

Participants

5

Reactant 2

HCID 6077842-(Tributylstannyl)pyridineHCID 86627426HCID 86627426, compound

Product 1

HCID 16071782HCID 16071782, compoundYield 48.1%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 7237O-XyleneSolvent

Procedure

An oven dried resealable Schlenk tube was charged with N-[6-chloro-5-(3-chloropyridin-4-yl)pyrazin-2-yl]cyclopropanecarboxamide (0.2 g, 0.65 mmol), 2-(tributylstannyl)pyridine (0.38 g, 1.04 mmol) and xylene (4 mL). The Schienk tube was subjected to three cycles of evacuation-backfilling with argon, and tetrakis(triphenylphosphine)palladium (75 mg, 0.065 mmol) was added. After three new cycles of evacuation-backfilling with argon, the Schlenk tube was capped and placed in a 150° C. oil bath. After 20 h, the mixture was cooled, partitioned between water and ethyl acetate, the aqueous phase was extracted twice with ethyl acetate, the organic layers washed with brine, dried (MgSO4) and evaporated. Silica gel flash chromatography (98:2 dichloromethane/methanol) furnished the title compound of Example 22 as a light brown solid (110 mg, 48%).

Workup

  1. customAn oven dried resealable Schlenk tube
  2. additionwas added
  3. customAfter three new cycles of evacuation-backfilling with argon, the Schlenk tube was capped
  4. customplaced in a 150° C.
  5. temperaturethe mixture was cooled
  6. custompartitioned between water and ethyl acetate
  7. extractionthe aqueous phase was extracted twice with ethyl acetate
  8. washthe organic layers washed with brine
  9. dry with materialdried (MgSO4)
  10. customevaporated

Sources & evidence

ORD record
ord-ed4732a280544ce387743d2684222a82
Source dataset
uspto-grants-2010_09
Patent number
US07790728B2

Reaction notes

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