Potassium Carbonate → HCID 70980542, compound

HRID 1475488Notes

Reaction equation

HRID 1475488 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5](B2OC(C)(C)C(C)(C)O2)[CH:4]=[N:3]1.[C:16]([O:20][C:21]([N:23]1[C:31]2[CH:30]=[C:29](Cl)[N:28]=[CH:27][C:26]=2[C:25]([CH3:34])([CH3:33])[CH2:24]1)=[O:22])([CH3:19])([CH3:18])[CH3:17].C(=O)([O-])[O-].[K+].[K+].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O.O1CCOCC1>[C:16]([O:20][C:21]([N:23]1[C:31]2[CH:30]=[C:29]([C:5]3[CH:4]=[N:3][N:2]([CH3:1])[CH:6]=3)[N:28]=[CH:27][C:26]=2[C:25]([CH3:34])([CH3:33])[CH2:24]1)=[O:22])([CH3:19])([CH3:17])[CH3:18]

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 27739871-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 86723969tert-Butyl 6-chloro-3,3-dimethyl-2,3-dihydro-1H-pyrrolo[3,2-c]pyridine-1-carboxylate

Product 1

HCID 70980542HCID 70980542, compoundYield 81.3%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 1-methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazole (0.609 g, 3.0 mmol), 6-chloro-3,3-dimethyl-2,3-dihydro-pyrrolo[3,2-c]pyridine-1-carboxylic acid tert-butyl ester (0.282 g, 1.0 mmol), potassium carbonate (0.414 g, 3.0 mmol), tris(dibenzylideneacetone)-dipalladium (0) (0.091 g, 0.1 mmol) and 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (SPhos, 0.041 g, 0.1 mmol), 1,4-dioxane (6 mL) and water (1.5 mL) was heated at 90° C. for 18 h. The solvent was evaporated, water (30 mL) was added and the product extracted with EtOAc (3×20 mL). Combined organic extracts were dried (MgSO4) and evaporated in vacuo to give an oil. Chromatography (SiO2; gradient elution with 0-100% EtOAc in 40-60 petroleum ether) gave the title compound (0.267 g) as an oil. MS: [M+H]+=329.

Workup

  1. customThe solvent was evaporated
  2. additionwater (30 mL) was added
  3. extractionthe product extracted with EtOAc (3×20 mL)
  4. dry with materialCombined organic extracts were dried (MgSO4)
  5. customevaporated in vacuo
  6. customto give an oil
  7. washChromatography (SiO2; gradient elution with 0-100% EtOAc in 40-60 petroleum ether)

Sources & evidence

ORD record
ord-990fb698162a465aa53400adadc48baf
Source dataset
uspto-grants-2015_04
Patent number
US09018214B2

Reaction notes

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