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

HRID 1037420
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HRID 1037420 반응식
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
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 178514306
HCID 178514306, 화합물
촉매
HCID 312751,4-Dioxane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-bc43bf3511604cc0a9417913b1be7a5d
출처 데이터셋
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08546376B2

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