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Dimethylacetamide → HCID 89700014, 화합물

HRID 1055753
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HRID 1055753 반응식
[C:1]([C:5]1[CH:6]=[C:7]([CH:32]=[C:33](Cl)[N:34]=1)[C:8]([NH:10][C:11]1[CH:16]=[CH:15][C:14]([CH3:17])=[C:13]([N:18]2[C:25]3[N:21]([N:22]=[C:23]([C:26]4[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=4)[CH:24]=3)[CH:20]=[CH:19]2)[CH:12]=1)=[O:9])([CH3:4])([CH3:3])[CH3:2].C(P(C(C)(C)C)C1C=CC2C(=CC=CC=2)C=1C1C2C(=CC=CC=2)C=CC=1)(C)(C)C.[CH3:65][N:66](C)C(=O)C>C(OCC)(=O)C.FC(F)(F)C([O-])=O.[Pd+2].FC(F)(F)C([O-])=O.[Zn].[C-]#N.[Zn+2].[C-]#N>[C:1]([C:5]1[CH:6]=[C:7]([CH:32]=[C:33]([C:65]#[N:66])[N:34]=1)[C:8]([NH:10][C:11]1[CH:16]=[CH:15][C:14]([CH3:17])=[C:13]([N:18]2[C:25]3[N:21]([N:22]=[C:23]([C:26]4[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=4)[CH:24]=3)[CH:20]=[CH:19]2)[CH:12]=1)=[O:9])([CH3:4])([CH3:3])[CH3:2]
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참가 물질

8

반응물 3

HCID 31374DimethylacetamideHCID 2734941(1,1'-Binaphthalen)-2-yldi-tert-butylphosphineHCID 89699945HCID 89699945, 화합물

생성물 1

HCID 89700014HCID 89700014, 화합물

시약·촉매·용매 4

HCID 11186Zinc cyanide (Zn(CN)2)촉매HCID 23994Zinc
촉매
HCID 2733347Palladium(II) trifluoroacetate촉매
HCID 8857Ethyl Acetate용매

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온도
95 °C

실험 절차

Under argon, a mixture of 137 mg (0.28 mmol) of the compound of Example 65, 4.04 mg (0.012 mmol) of palladium(II) trifluoroacetate, 9.91 mg (0.025 mmol) of racemic 2-di-tert-butylphosphino-1,1′-binaphthyl, 3.51 mg (0.054 mmol) of zinc flakes and 18.6 mg (0.16 mmol) of zinc cyanide in 1.5 ml N,N-dimethylacetamide was stirred at 95° C. for 20 hours. After cooling, the mixture was diluted with 80 ml of ethyl acetate and the mixture was washed in each case once with 10 ml of water and 10 ml saturated sodium chloride solution. The organic phase was dried over sodium sulphate and, after filtration, concentrated under reduced pressure. The residue obtained in this manner was purified by chromatography on a Biotage system (25 g Snap column; mobile phase gradient ethyl acetate/hexane, starting with 70% ethyl acetate, then increasing rapidly to 100% ethyl acetate). Further purification was by preparative thick-layer chromatography (2 mm layer thickness with concentration zone, mobile phase ethyl acetate, elution with methylene chloride/methanol 7:3). This gave 56 mg (38% of theory) of the title compound.

후처리

  1. temperatureAfter cooling
  2. washthe mixture was washed in each case once with 10 ml of water and 10 ml saturated sodium chloride solution
  3. dry with materialThe organic phase was dried over sodium sulphate
  4. filtrationafter filtration
  5. concentrationconcentrated under reduced pressure
  6. customThe residue obtained in this manner
  7. customwas purified by chromatography on a Biotage system (25 g Snap column
  8. temperatureincreasing rapidly to 100% ethyl acetate)
  9. customFurther purification
  10. concentrationwas by preparative thick-layer chromatography (2 mm layer thickness with concentration zone, mobile phase ethyl acetate, elution with methylene chloride/methanol 7:3)

출처 및 근거

ORD 기록
ord-e7f88f5b5e144a79b254d62dd1ac8cf0
출처 데이터셋
uspto-grants-2016_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09394309B2

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