5-Tributylstannyl-1H-pyrazole-3-carboxylic acid ethyl ester → HCID 178468658, compound

HRID 906221Notes

Reaction equation

HRID 906221 reaction equation
C([Sn](CCCC)(CCCC)[C:6]1[NH:10][N:9]=[C:8]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:7]=1)CCC.Br[C:25]1[N:30]2[N:31]=[CH:32][N:33]=[C:29]2[C:28]([NH:34][C:35]2[CH:40]=[CH:39][C:38]([N:41]3[CH2:46][C@@H:45]4[CH2:47][C@H:42]3[CH2:43][N:44]4[CH:48]([CH3:50])[CH3:49])=[CH:37][CH:36]=2)=[N:27][CH:26]=1>C1COCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH:48]([N:44]1[CH2:43][C@@H:42]2[CH2:47][C@H:45]1[CH2:46][N:41]2[C:38]1[CH:37]=[CH:36][C:35]([NH:34][C:28]2[C:29]3[N:30]([N:31]=[CH:32][N:33]=3)[C:25]([C:6]3[NH:10][N:9]=[C:8]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:7]=3)=[CH:26][N:27]=2)=[CH:40][CH:39]=1)([CH3:50])[CH3:49]

Participants

5

Reactant 2

HCID 149720685-Tributylstannyl-1H-pyrazole-3-carboxylic acid ethyl esterHCID 57963946(5-bromo-[1,2,4]triazolo[1,5-a]pyrazin-8-yl)-[4-((1S,4S)-5-isopropyl-2,5-diazabicyclo[2.2.1]hept-2-yl)-phenyl]amine

Product 1

HCID 178468658HCID 178468658, compoundYield 28.7%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of ethyl 5-(tributylstannyl)-1H-pyrazole-3-carboxylate (109.0 mg, 0.25 mmol) (Heterocyles, 1992, 813-818), (5-bromo-[1,2,4]triazolo[1,5-a]pyrazin-8-yl)-[4-((1S,4S)-5-isopropyl-2,5-diazabicyclo[2.2.1]hept-2-yl)-phenyl]amine (163.0 mg, 0.38 mmol), and Pd(PPh3)2Cl2 (27.0 mg, 0.04 mmol) in THF (3 mL) is refluxed for 18 hours. After return to room temperature, solvent is removed under reduced pressure. Purification of the residue by silica gel column chromatography eluting with a mixture of DCM/7N NH3 in methanol (97/3) affords the title compound (35.0 mg, 28%).

Workup

  1. temperatureis refluxed for 18 hours
  2. customAfter return to room temperature, solvent is removed under reduced pressure
  3. customPurification of the residue by silica gel column chromatography
  4. washeluting with a mixture of DCM/7N NH3 in methanol (97/3)

Sources & evidence

ORD record
ord-7e2235aed0fa400fbc80c74f1675e617
Source dataset
uspto-grants-2011_09
Patent number
US08012983B2

Reaction notes

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