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Cesium carbonate → HCID 59233383, 화합물

HRID 1400087
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HRID 1400087 반응식
Br[C:2]1[N:3]=[N:4][C:5]([C:10]([F:13])([F:12])[F:11])=[CH:6][C:7]=1[O:8][CH3:9].[C:14]([O:18][C:19]([N:21]1[CH2:26][CH2:25][CH:24]([NH2:27])[CH2:23][CH2:22]1)=[O:20])([CH3:17])([CH3:16])[CH3:15].C(=O)([O-])[O-].[Cs+].[Cs+].C1C=CC(P(C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:14]([O:18][C:19]([N:21]1[CH2:26][CH2:25][CH:24]([NH:27][C:2]2[N:3]=[N:4][C:5]([C:10]([F:13])([F:12])[F:11])=[CH:6][C:7]=2[O:8][CH3:9])[CH2:23][CH2:22]1)=[O:20])([CH3:17])([CH3:15])[CH3:16]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 10796Cesium carbonateHCID 634876Binap, (A+-)-HCID 12682914-Amino-1-Boc-piperidineHCID 592333823-Bromo-4-methoxy-6-(trifluoromethyl)pyridazine

생성물 1

HCID 59233383HCID 59233383, 화합물수율 63.2%

시약·촉매·용매 2

HCID 167845
palladium(II) acetate
촉매
HCID 1140Toluene용매

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온도
110 °C

실험 절차

To a stirred solution of 3-bromo-4-methoxy-6-trifluoromethyl-pyridazine (D6) (0.79 g, 3.07 mmol), 4-amino-piperidine-1-carboxylic acid tert-butyl ester (0.74 g, 3.69 mmol) and cesium carbonate (2.0 g, 6.14 mmol) in toluene (15 ml) in a sealed tube under nitrogen, were added (R)-(+)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (0.29 g, 0.46 mmol) and palladium(II) acetate (0.034 g, 0.15 mmol). The reactiom mixture was stirred at 110° C. for 18 h. After cooling to room temperature, the reaction mixture was filtered though Celite and the filtrate was evaporated. The crude product was purified by flash column chromatography (silica gel; 3% ammonia in methanol (7M)/dichloromethane). The desired fractions were collected and evaporated in vacuo. to yield D7 (0.73 g, 63%) as a yellow solid. C16H23F3N4O3 requires 376; Found 377 (MH+).

후처리

  1. temperatureAfter cooling to room temperature
  2. filtrationthe reaction mixture was filtered though Celite
  3. customthe filtrate was evaporated
  4. customThe crude product was purified by flash column chromatography (silica gel; 3% ammonia in methanol (7M)/dichloromethane)
  5. customThe desired fractions were collected
  6. customevaporated in vacuo

출처 및 근거

ORD 기록
ord-7df0ef6da96c4be39665fc50b5f4f2ba
출처 데이터셋
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08906921B2

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