Potassium Carbonate → tert-butyl 1-(4-(8-methyl-4-oxo-2-phenyl-4H-pyrano[2,3-c]pyridin-3-yl)phenyl)cyclobutylcarbamate

HRID 1037420Notes

Reaction equation

HRID 1037420 reaction equation
Cl[C:2]1[N:3]=[CH:4][CH:5]=[C:6]2[C:11](=[O:12])[C:10]([C:13]3[CH:18]=[CH:17][C:16]([C:19]4([NH:23][C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])[CH2:22][CH2:21][CH2:20]4)=[CH:15][CH:14]=3)=[C:9]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[O:8][C:7]=12.[CH3:37]B(O)O.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.N#N.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:37][C:2]1[N:3]=[CH:4][CH:5]=[C:6]2[C:11](=[O:12])[C:10]([C:13]3[CH:18]=[CH:17][C:16]([C:19]4([NH:23][C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:27])[CH3:28])[CH2:20][CH2:21][CH2:22]4)=[CH:15][CH:14]=3)=[C:9]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[O:8][C:7]=12

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 139377Methylboronic AcidHCID 86671031tert-Butyl 1-(4-(8-chloro-4-oxo-2-phenyl-4H-pyrano[2,3-c]pyridin-3-yl)phenyl)cyclobutylcarbamate

Product 1

HCID 67068031tert-butyl 1-(4-(8-methyl-4-oxo-2-phenyl-4H-pyrano[2,3-c]pyridin-3-yl)phenyl)cyclobutylcarbamateYield 42%

Reagents, catalysts & solvents 2

HCID 178514306HCID 178514306, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

tert-Butyl 1-(4-(8-chloro-4-oxo-2-phenyl-4H-pyrano[2,3-c]pyridin-3-yl)phenyl)cyclobutylcarbamate (50.3 mg, 0.1 mmol) was dissolved in 1,4-dioxane (5 mL). Methyl boronic acid (8.98 mg, 0.15 mmol) and potassium carbonate (41.5 mg, 0.3 mmol) were added. The solution was degassed, flushing with nitrogen tetrakis (11.56 mg, 0.01 mmol) was added and the solution was refluxed for 24 h. The reaction mixture was filtered, washed with ethyl acetate and evaporated. The crude product was purified by column chromatography using hex and ethyl acetate (0-65%) to give the title compound (20 mg, 42%). LCMS (Method I): RT=7.40 min, [M+H]+=483.

Workup

  1. customThe solution was degassed
  2. additionwas added
  3. temperaturethe solution was refluxed for 24 h
  4. filtrationThe reaction mixture was filtered
  5. washwashed with ethyl acetate
  6. customevaporated
  7. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-bc43bf3511604cc0a9417913b1be7a5d
Source dataset
uspto-grants-2013_10
Patent number
US08546376B2

Reaction notes

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