Potassium Carbonate → HCID 86724021, compound

HRID 1475446Notes

Reaction equation

HRID 1475446 reaction equation
[CH3:1][C:2]1(C)[C:6](C)([CH3:7])OB(C(=C)CC)O1.[C:14]([O:18][C:19]([N:21]1[C:29]2[CH:28]=[C:27](Cl)[N:26]=[CH:25][C:24]=2[C:23]([CH3:32])([CH3:31])[CH2:22]1)=[O:20])([CH3:17])([CH3:16])[CH3:15].C(=O)([O-])[O-].[K+].[K+].C([O-])(O)=O.[Na+]>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].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1.O.O1CCOCC1>[C:14]([O:18][C:19]([N:21]1[C:29]2[CH:28]=[C:27]([C:2](=[CH2:1])[CH2:6][CH3:7])[N:26]=[CH:25][C:24]=2[C:23]([CH3:32])([CH3:31])[CH2:22]1)=[O:20])([CH3:17])([CH3:16])[CH3:15]

Participants

9

Reactant 4

HCID 11430Potassium CarbonateHCID 516892Sodium BicarbonateHCID 86723969tert-Butyl 6-chloro-3,3-dimethyl-2,3-dihydro-1H-pyrrolo[3,2-c]pyridine-1-carboxylateHCID 867240221403904-88-0

Product 1

HCID 86724021HCID 86724021, compoundYield 55.5%

Reagents, catalysts & solvents 4

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
94 °C

Procedure

A mixture of 4,4,5,5-tetramethyl-2-(1-methylene-propyl)-[1,3,2]dioxaborolane (0.793 g, 4.36 mmol), 6-chloro-3,3-dimethyl-2,3-dihydro-1H-pyrrolo[3,2-c]pyridine-1-carboxylic acid tert-butyl ester (0.821 g, 2.9 mmol), potassium carbonate (1.20 g, 8.7 mmol), tris(dibenzylideneacetone)-dipalladium (0) (0.133 g, 0.145 mmol), 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (SPhos, 0.060 g, 0.145 mmol), 1,4-dioxane (18 mL) and water (45 mL) was heated at 94° C. for 18 h, then poured into saturated aqueous NaHCO3 (100 mL) and extracted with DCM (3×50 mL). Combined organic extracts were dried (Na2SO4) and evaporated in vacuo to give an oil. Chromatography (SiO2; gradient elution with 0-25% Et2O in 40-60 petroleum ether) gave the title compound (0.487 g) as an oil. MS: [M+H]+=303. Further chromatography of mixed fractions gave further title compound (0.20 g).

Workup

  1. extractionextracted with DCM (3×50 mL)
  2. dry with materialCombined organic extracts were dried (Na2SO4)
  3. customevaporated in vacuo
  4. customto give an oil
  5. washChromatography (SiO2; gradient elution with 0-25% Et2O in 40-60 petroleum ether)

Sources & evidence

ORD record
ord-de691348507a47e2975675ce9cd8d01e
Source dataset
uspto-grants-2015_04
Patent number
US09018214B2

Reaction notes

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