Cesium carbonate → HCID 66977630, compound

HRID 77091Notes

Reaction equation

HRID 77091 reaction equation
C(OC([N:8]1[C:12]2[CH:13]=[N:14][CH:15]=[CH:16][C:11]=2[N:10]=[C:9]1[C:17]1[CH:22]=[C:21](Br)[CH:20]=[CH:19][C:18]=1[Cl:24])=O)(C)(C)C.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1.C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:65]([O:67][C:68]([CH:70]1[CH2:75][CH2:74][NH:73][CH2:72][CH2:71]1)=[O:69])[CH3:66]>[Pd].[Pd].C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.O1CCOCC1>[CH2:65]([O:67][C:68]([CH:70]1[CH2:75][CH2:74][N:73]([C:21]2[CH:20]=[CH:19][C:18]([Cl:24])=[C:17]([C:9]3[NH:8][C:12]4[CH:13]=[N:14][CH:15]=[CH:16][C:11]=4[N:10]=3)[CH:22]=2)[CH2:72][CH2:71]1)=[O:69])[CH3:66]

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 70770Ethyl 4-piperidinecarboxylateHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 66977629HCID 66977629, compound

Product 1

HCID 66977630HCID 66977630, compoundYield 126.7%

Reagents, catalysts & solvents 2

HCID 9832798Tris(dibenzylideneacetone) dipalladiumCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

Method C—Step d 2-(5-Bromo-2-chloro-phenyl)-imidazo[4,5-c]pyridine-3-carboxylic acid tert-butyl ester (0.50 g, 1.23 mmol), tris(dibenzylideneacetone) dipalladium(0) (Pd2 dba3) (0.13 g, 0.18 mmol), 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl (Xphos) (0.17 g, 0.37 mmol) and cesium carbonate (1.20 g, 3.68 mmol) were placed into a dried schlenk and few cycles of vacuum/nitrogen were performed. Then dry dioxane (2.00 mL) and piperidine-4-carboxylic acid ethyl ester (0.38 mL, 2.45 mmol) were added, the reaction mixture was heated at 80° C. for 4 h, left cooling to room temperature and filtered through sodium sulphate (Na2SO4). The crude was purified by flash chromatography (eluent gradient: EtOAc 100% to EtOAc:MeOH/95:5), to obtain 0.60 g of a mixture of the title compound and the starting material deprotected (7:3). The mixture was used for the next step.

Workup

  1. customwere placed into a dried schlenk
  2. waitleft
  3. temperaturecooling to room temperature
  4. filtrationfiltered through sodium sulphate (Na2SO4)
  5. customThe crude was purified by flash chromatography (eluent gradient: EtOAc 100% to EtOAc:MeOH/95:5)

Sources & evidence

ORD record
ord-9b1bdda81b164d6fab156694a468f254
Source dataset
uspto-grants-2014_09
Patent number
US08835648B2

Reaction notes

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