Ethyl Acetate → HCID 71212808, compound

HRID 513201Notes

Reaction equation

HRID 513201 reaction equation
CC1(C)C(C)(C)OB([C:9]2[CH:10]=[N:11][N:12]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH:13]=2)O1.Br[C:23]1[CH:24]=[C:25]2[C:29](=[CH:30][CH:31]=1)[NH:28][CH:27]=[CH:26]2.[F-].[Cs+].CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C.[CH3:68][CH2:69][O:70][C:71](C)=[O:72]>O1CCOCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:17]([O:16][C:14]([N:12]1[CH:13]=[C:9]([C:23]2[CH:24]=[C:25]3[C:29](=[CH:30][CH:31]=2)[NH:28][C:27]([C:71]([O:70][CH2:69][CH3:68])=[O:72])=[CH:26]3)[CH:10]=[N:11]1)=[O:15])([CH3:18])([CH3:19])[CH3:20]

Participants

8

Reactant 5

HCID 8857Ethyl AcetateHCID 249055-BromoindoleHCID 25953Cesium fluorideHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 16217654tert-butyl 4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole-1-carboxylate

Product 1

HCID 71212808HCID 71212808, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 312751,4-DioxaneSolvent

Procedure

To a degassed solution of tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole-1-carboxylate (138 mg, 0.47 mmol), 5-bromo-indole (63 mg, 0.24 mmol), CsF (107 mg, 0.71 mmol), and X-Phos (11.2 mg, 0.023 mmol) in dioxane (2 mL) was added palladium acetate (2.6 mg, 0.012 mmol) under nitrogen. The mixture was then heated to 90 C overnight, cooled to r.t., and diluted with EtOAc. Following filtration and concentration in vacuo, the residue was purified on silica (0-30% EtOAc/hexanes) to yield the title product.

Workup

  1. temperatureThe mixture was then heated to 90 C overnight
  2. filtrationfiltration and concentration in vacuo
  3. customthe residue was purified on silica (0-30% EtOAc/hexanes)

Sources & evidence

ORD record
ord-cb0a3fb552174cea9fabdcf44e951fba
Source dataset
uspto-grants-2015_08
Patent number
US09102673B2

Reaction notes

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