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

HRID 1037429ノート

反応式

HRID 1037429 の反応式
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]

参加物

7

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 11186Zinc cyanide (Zn(CN)2)触媒HCID 23994Zinc触媒HCID 2733347Palladium(II) trifluoroacetate触媒

反応条件

温度
95 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-71677fc2a6bd4113bb0aaf2119b02cc4
出典データセット
uspto-grants-2013_10
特許番号
US08546376B2

反応ノート

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