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

HRID 1037429노트

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HRID 1037429 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.C1(C2C3C(=CC=CC=3)C=CC=2)C2C(=CC=CC=2)C=CC=1.C(PC(C)(C)C)(C)(C)C.C[C:67]([N:69](C)C)=O>[C-]#N.[Zn+2].[C-]#N.FC(F)(F)C([O-])=O.[Pd+2].FC(F)(F)C([O-])=O.[Zn]>[C:67]([C:2]1[N:3]=[CH:4][CH:5]=[C:6]2[C:11](=[O:12])[C:10]([C:13]3[CH:14]=[CH:15][C:16]([C:19]4([NH:23][C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])[CH2:20][CH2:21][CH2:22]4)=[CH:17][CH:18]=3)=[C:9]([C:31]3[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=3)[O:8][C:7]=12)#[N:69]

참가 물질

7

반응물 3

HCID 31374DimethylacetamideHCID 66906061HCID 66906061, 화합물HCID 86671031tert-Butyl 1-(4-(8-chloro-4-oxo-2-phenyl-4H-pyrano[2,3-c]pyridin-3-yl)phenyl)cyclobutylcarbamate

생성물 1

HCID 68227519tert-butyl 1-(4-(8-cyano-4-oxo-2-phenyl-4H-pyrano[2,3-c]pyridin-3-yl)phenyl)cyclobutylcarbamate수율 61%

시약·촉매·용매 3

HCID 11186Zinc cyanide (Zn(CN)2)촉매HCID 23994Zinc촉매HCID 2733347Palladium(II) trifluoroacetate촉매

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온도
95 °C

실험 절차

tert-Butyl (1-(4-(8-chloro-4-oxo-2-phenyl-4H-pyrano[2,3-c]pyridin-3-yl)phenyl)cyclobutyl)carbamate (50 mg, 0.1 mmol), zinc (II) cyanide (38 mg, 0.058 mmol) and binaphthyl-di-tert-butyl phosphine (4 mg, 0.01 mmol), palladium(II) trifluoroacetate (4 mg, 0.01 mmol), zinc dust (2 mg) were suspended in DMA (1 mL) in a microwave vial. The vial was sealed, evacuated and flushed twice with nitrogen. The reaction mixture was heated at 95° C. for 18 h. The resulting mixture was allowed to cool to RT, partitioned between ethyl acetate (40 mL) and water (20 mL) and the phases were separated. The organic layer was washed with brine (2 mL), dried (Na2SO4), filtered and concentrated in vacuo. The resulting residue was subjected to flash chromatography (SiO2, 50% ethyl acetate in cyclohexane) to afford the title compound (30 mg, 61%). LCMS (Method I): RT=7.63 min, [M+H]+=438 (-tBu), [M+Na]+=516.

후처리

  1. customThe vial was sealed
  2. customevacuated
  3. customflushed twice with nitrogen
  4. temperatureto cool to RT
  5. custompartitioned between ethyl acetate (40 mL) and water (20 mL)
  6. customthe phases were separated
  7. washThe organic layer was washed with brine (2 mL)
  8. dry with materialdried (Na2SO4)
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-71677fc2a6bd4113bb0aaf2119b02cc4
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08546376B2

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