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Cesium carbonate → HCID 54591302, 화합물

HRID 1260187
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HRID 1260187 반응식
Br[C:2]1[CH:3]=[C:4]([CH:28]=[CH:29][CH:30]=1)[CH2:5][N:6]1[C:10]([CH3:11])=[CH:9][C:8]([C:12]2[O:16][N:15]=[C:14]([C:17]3[CH:22]=[CH:21][C:20]([O:23][C:24]([F:27])([F:26])[F:25])=[CH:19][CH:18]=3)[N:13]=2)=[N:7]1.[Si]([O:48][CH:49]1[CH2:52][NH:51][CH2:50]1)(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O>[CH3:11][C:10]1[N:6]([CH2:5][C:4]2[CH:3]=[C:2]([N:51]3[CH2:52][CH:49]([OH:48])[CH2:50]3)[CH:30]=[CH:29][CH:28]=2)[N:7]=[C:8]([C:12]2[O:16][N:15]=[C:14]([C:17]3[CH:22]=[CH:21][C:20]([O:23][C:24]([F:27])([F:26])[F:25])=[CH:19][CH:18]=3)[N:13]=2)[CH:9]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 4

HCID 10796Cesium carbonateHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 178425313-((Tert-butyldiphenylsilyl)oxy)azetidineHCID 58072149HCID 58072149, 화합물

생성물 1

HCID 54591302HCID 54591302, 화합물

시약·촉매·용매 3

HCID 9811564
Bis(dibenzylideneacetone)palladium
촉매
HCID 962Water용매
HCID 6228Dimethylformamide용매

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온도
120 °C

실험 절차

A mixture of 2.0 g (4.17 mmol) of the compound from Example 1A, 1.95 g (6.26 mmol) of the compound from Example 8A, 256 mg (0.280 mmol) of tris(dibenzylideneacetone)dipalladium(0), 398 mg (0.835 mmol) of 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl (X-Phos) and 2.72 g (8.35 mmol) of caesium carbonate in 20 ml of anhydrous DMF was heated to 120° C. under argon in a microwave oven (Biotage Initiator, dynamic control of the incident power) for 2.5 h. After cooling to RT, 100 ml of water were added to the reaction mixture, which was extracted three times with approx. 100 ml each time of ethyl acetate. The combined organic extracts were washed successively with water and saturated sodium chloride solution, dried over anhydrous magnesium sulphate, filtered and finally freed of the solvent on a rotary evaporator. The remaining residue was dissolved in 40 ml of THF, and 6.3 ml (6.26 mmol) of a 1 M solution of tetra-n-butylammonium fluoride (TBAF) in THF were added. After this mixture had been stirred at RT for 1 h, it was subjected to aqueous workup in the same way as described above. The remaining residue was purified by suction filtration through 200 g of silica gel with 2:1 (3 liters)→1:1 (3 liters) cyclohexane/ethyl acetate as the eluent. After concentration and drying under a high vacuum, 1.56 g (79% of theory) of the title compound were obtained.

후처리

  1. temperatureAfter cooling to RT
  2. extractionwas extracted three times with approx. 100 ml each time of ethyl acetate
  3. washThe combined organic extracts were washed successively with water and saturated sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulphate
  5. filtrationfiltered
  6. customfinally freed of the solvent on a rotary evaporator
  7. dissolutionThe remaining residue was dissolved in 40 ml of THF
  8. addition6.3 ml (6.26 mmol) of a 1 M solution of tetra-n-butylammonium fluoride (TBAF) in THF were added
  9. filtrationThe remaining residue was purified by suction filtration through 200 g of silica gel with 2:1 (3 liters)→1
  10. concentrationAfter concentration
  11. dry with materialdrying under a high vacuum, 1.56 g (79% of theory) of the title compound
  12. customwere obtained

출처 및 근거

ORD 기록
ord-ffdac2a497b742619e9f3bd0c3e1acfd
출처 데이터셋
uspto-grants-2013_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08470811B2

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