Cesium carbonate → HCID 89666690, compound

HRID 2171233Notes

Reaction equation

HRID 2171233 reaction equation
[C:1](=[O:8])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])[NH2:2].C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.Br[C:58]1[CH:63]=[N:62][CH:61]=[C:60]2[N:64]([CH2:67][CH3:68])[N:65]=[CH:66][C:59]=12>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].C(OCC)(=O)C.O1CCOCC1>[CH2:67]([N:64]1[C:60]2=[CH:61][N:62]=[CH:63][C:58]([NH:2][C:1](=[O:8])[O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[C:59]2[CH:66]=[N:65]1)[CH3:68]

Participants

8

Reactant 4

HCID 10796Cesium carbonateHCID 77922tert-Butyl carbamateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 57606802HCID 57606802, compound

Product 1

HCID 89666690HCID 89666690, compoundYield 84.7%

Reagents, catalysts & solvents 3

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

Procedure

tert-Butyl carbamate (90 mg), cesium carbonate (500 mg), Pd2(dba)3 (46 mg), and Xantphos (58 mg) were added to a dioxane solution (2 ml) containing 4-bromo-1-ethyl-1H-pyrazolo[3,4-c]pyridine (115 mg) obtained in the 1st step, followed by microwave irradiation (Initiator™, 130° C., 1 hour, 2.45 GHz, 0-240 W). Ethyl acetate was added to the reaction solution, insoluble matter was removed by filtration, and the solvent was distilled away under reduced pressure. The obtained residue was purified by silica gel chromatography (n-hexane:ethyl acetate=1:0 to 3:1). A white solid of tert-butyl (1-ethyl-1H-pyrazolo[3,4-c]pyridin-4-yl)carbamate (113 mg) was thus obtained.

Workup

  1. customobtained in the 1st step
  2. customfollowed by microwave irradiation (Initiator™, 130° C., 1 hour, 2.45 GHz, 0-240 W)
  3. customwas removed by filtration
  4. distillationthe solvent was distilled away under reduced pressure
  5. customThe obtained residue was purified by silica gel chromatography (n-hexane:ethyl acetate=1:0 to 3:1)

Sources & evidence

ORD record
ord-6cad7cb818354909a2949277eeeab10f
Source dataset
uspto-grants-2015_06
Patent number
US09051310B2

Reaction notes

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