5-(Tributylstannyl)-2-(triisopropylsilyl)-1,3-oxazole → N-[6-(1,3-oxazol-5-yl)-5-pyridin-4-ylpyrazin-2-yl]cyclopropanecarboxamide

HRID 1710700Notes

Reaction equation

HRID 1710700 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][CH:15]=1.C([Sn](CCCC)(CCCC)[C:25]1[O:29][C:28]([Si](C(C)C)(C(C)C)C(C)C)=[N:27][CH:26]=1)CCC>C1(C)C(C)=CC=CC=1.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>[O:29]1[C:25]([C:2]2[N:7]=[C:6]([NH:8][C:9]([CH:11]3[CH2:13][CH2:12]3)=[O:10])[CH:5]=[N:4][C:3]=2[C:14]2[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=2)=[CH:26][N:27]=[CH:28]1

Participants

5

Reactant 2

HCID 114971955-(Tributylstannyl)-2-(triisopropylsilyl)-1,3-oxazoleHCID 59457608N-(6-Chloro-5-pyridin-4-ylpyrazin-2-yl)cyclopropanecarboxamide

Product 1

HCID 53325341N-[6-(1,3-oxazol-5-yl)-5-pyridin-4-ylpyrazin-2-yl]cyclopropanecarboxamideYield 35%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 7237O-XyleneSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of N-(6-chloro-5-pyridin-4-ylpyrazin-2-yl)cyclopropanecarboxamide (100 mg, 0.36 mmol) and 5-(tributylstannyl)-2-(triisopropylsilyl)-1,3-oxazole (397 mg, 0.73 mmol) in xylene (3 mL) was degassed with argon. The catalyst Pd(PPh3)4 (25 mg, 0.022 mmol, 6 mol %) was added and degassing was repeated. The mixture was heated to 90° C. in a sealed tube and stirred overnight. The mixture was cooled and ethyl acetate and HCl 2N were added. The aqueous layer was washed with ethyl acetate and then neutralized with 6N NaOH. The cloudy solution was extracted with CH2Cl2. The organic layer was dried and concentrated. The residue was purified by flash silica gel chromatography (dichloromethane/methanol 95:5) to give the title compound (36 mg, 35%) as a white solid.

Workup

  1. customwas degassed with argon
  2. customdegassing
  3. temperatureThe mixture was cooled
  4. additionethyl acetate and HCl 2N were added
  5. washThe aqueous layer was washed with ethyl acetate
  6. extractionThe cloudy solution was extracted with CH2Cl2
  7. customThe organic layer was dried
  8. concentrationconcentrated
  9. customThe residue was purified by flash silica gel chromatography (dichloromethane/methanol 95:5)

Sources & evidence

ORD record
ord-526f9712a73f41bea9e7839067aa4219
Source dataset
uspto-grants-2010_09
Patent number
US07790728B2

Reaction notes

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