Potassium Carbonate → HCID 59276285, compound

HRID 2070913Notes

Reaction equation

HRID 2070913 reaction equation
[CH3:1][C:2]1([CH3:37])[C:10]2[C:5](=[CH:6][C:7]([NH:11][C:12]3[N:28]=[C:15]4[CH:16]=[CH:17][CH:18]=[C:19]([C:20]([CH:22]5[CH2:27][CH2:26][O:25][CH2:24][CH2:23]5)=O)[N:14]4[N:13]=3)=[CH:8][CH:9]=2)[N:4](C(OC(C)(C)C)=O)[C:3]1=[O:36].[C:38]1(P(C2C=CC=CC=2)C2C3OC4C(=CC=CC=4P(C4C=CC=CC=4)C4C=CC=CC=4)C(C)(C)C=3C=CC=2)C=CC=CC=1.NC1C=C2C(C(C)(C)C(=O)N2C(OC(C)(C)C)=O)=CC=1.BrC1N=C2C=CC=C(C(C3CCOCC3)=O)N2N=1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.C(OCC)(=O)C.O.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]>[CH3:1][C:2]1([CH3:37])[C:10]2[C:5](=[CH:6][C:7]([NH:11][C:12]3[N:28]=[C:15]4[CH:16]=[CH:17][CH:18]=[C:19]([CH:20]([CH:22]5[CH2:23][CH2:24][O:25][CH2:26][CH2:27]5)[CH3:38])[N:14]4[N:13]=3)=[CH:8][CH:9]=2)[NH:4][C:3]1=[O:36]

Participants

10

Reactant 5

HCID 11430Potassium CarbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 50999069tert-Butyl 6-amino-3,3-dimethyl-2-oxo-2,3-dihydro-1H-indole-1-carboxylateHCID 67293423HCID 67293423, compoundHCID 86640820HCID 86640820, compound

Product 1

HCID 59276285HCID 59276285, compoundYield 67%

Reagents, catalysts & solvents 4

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

tert-Butyl 3,3-dimethyl-2-oxo-6-(5-(tetrahydro-2H-pyran-4-carbonyl)-[1,2,4]triazolo[1,5-a]pyridin-2-ylamino)indoline-1-carboxylate. A mixture of tris(dibenzylideneacetone)dipalladium(0) (0.050 g, 0.054 mmol) and 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (0.063 g, 0.109 mmol) in 1,4-dioxane (2 mL) was heated briefly with a heat gun until very hot and then added to tert-butyl 6-amino-3,3-dimethyl-2-oxoindoline-1-carboxylate (0.150 g, 0.543 mmol), (2-bromo-[1,2,4]triazolo[1,5-a]pyridin-5-yl)(tetrahydro-2H-pyran-4-yl)methanone (0.168 g, 0.543 mmol) and finely ground potassium carbonate (0.308 g, 2.226 mmol) in a sealable vessel with a stirbar. Nitrogen was blown in to blow out air. The resulting mixture was sealed, stirred vigorously, and heated at 100° C. for 1.5 h. After cooling to room temperature the reaction mixture was diluted with ethyl acetate and water with vigorous stirring. The resulting mixture was filtered through a syringe filter and the filter cake washed with ethyl acetate. The layers of the filtrate were separated in a reparatory funnel and the organics were concentrated on a rotary evaporator. The residue was taken up in dichloromethane and purified using flash chromatography (Biotage) (20-80% ethyl acetate in hexane) to give the desired product (0.183 g, 0.362 mmol, 67% yield) as a yellow solid. MS (ESI) m/z 506.2 [M+1]+.

Workup

  1. temperaturewas heated briefly with a heat gun until very hot and
  2. customThe resulting mixture was sealed
  3. temperatureAfter cooling to room temperature the reaction mixture
  4. filtrationThe resulting mixture was filtered through a syringe
  5. filtrationfilter
  6. washthe filter cake washed with ethyl acetate
  7. customThe layers of the filtrate were separated in a reparatory funnel
  8. concentrationthe organics were concentrated on a rotary evaporator
  9. custompurified

Sources & evidence

ORD record
ord-bed0ec9c9e584a768a1752d9474b4d1c
Source dataset
uspto-grants-2012_10
Patent number
US08299056B2

Reaction notes

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