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Dimethylformamide → HCID 15512895, 화합물

HRID 2305340
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HRID 2305340 반응식
CN(C)[CH:3]=[O:4].[CH3:6][O:7][C:8]([C:10]1[N:11]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=2[C:36]([F:39])([F:38])[F:37])[S:12](=[O:29])(=[O:28])[C:13]2[CH:27]=[CH:26][CH:25]=[CH:24][C:14]=2[C:15]=1OS(C(F)(F)F)(=O)=O)=[O:9].C(=O)([O-])[O-].[K+].[K+].[CH3:46][O:47][C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][C:49]=1B(O)O>C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Pd].C(OCC)C.C1(C)C=CC=CC=1>[CH3:6][O:7][C:8]([C:10]1[N:11]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=2[C:36]([F:38])([F:39])[F:37])[S:12](=[O:28])(=[O:29])[C:13]2[CH:27]=[CH:26][CH:25]=[CH:24][C:14]=2[C:15]=1[C:52]1[CH:53]=[C:48]([O:47][CH3:46])[CH:49]=[C:50]([O:4][CH3:3])[CH:51]=1)=[O:9]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 27339582-Methoxyphenylboronic acidHCID 11124297HCID 11124297, 화합물

생성물 1

HCID 15512895HCID 15512895, 화합물수율 83%

시약·촉매·용매 3

HCID 11979704
Tetrakis(triphenylphosphine)palladium
촉매
HCID 1140Toluene용매
HCID 3283Diethyl Ether용매

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온도
100 °C

실험 절차

To dimethylformamide (18 mL) was added 1,1-dioxo-4-(trifluoro-methanesulfonyloxy)-2-(2-trifluoromethyl-phenyl)-1,2-dihydro-1λ6-benzo[e][1,2]thiazine-3-carboxylic acid methyl ester, (1.60 g, 3.0 mmol), palladium tetrakis(triphenyl phosphine) (0.2 g, 0.17 mmol), potassium carbonate (0.7 g, 6.0 mmol), 2-methoxy-phenyl-boronic acid (0.88 g, 6.0 mmol), and toluene (50 mL). The mixture was heated to 100° C. for 30 minutes and was filtered through a pad of Celite. The filtrate and EtOAc washing solution was washed three times with saturated sodium bicarbonate solution, brine, and dried over charcoal and anhydrous magnesium sulfate. The suspension was filtered and stripped to an oil which was resuspended in ethyl acetate and ethyl ether. Insoluble material from this mixture was filtered off, and the filtrate was concentrated in vacuo to an oil. The residue was chromatographed on silica gel eluted with a mixture of ethyl acetate and hexane (25:75). The appropriate fractions were concentrated in vacuo and crystallized from ethyl ether giving a solid 1.29 g, 83% yield.

후처리

  1. filtrationwas filtered through a pad of Celite
  2. washThe filtrate and EtOAc washing solution was washed three times with saturated sodium bicarbonate solution, brine
  3. dry with materialdried over charcoal and anhydrous magnesium sulfate
  4. filtrationThe suspension was filtered
  5. filtrationInsoluble material from this mixture was filtered off
  6. concentrationthe filtrate was concentrated in vacuo to an oil
  7. customThe residue was chromatographed on silica gel
  8. washeluted with a mixture of ethyl acetate and hexane (25:75)
  9. concentrationThe appropriate fractions were concentrated in vacuo

출처 및 근거

ORD 기록
ord-1bcd9ffb00db43d1a944a33f6cfc64b4
출처 데이터셋
uspto-grants-2002_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06440962B2

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