Sodium Carbonate → 3-(1-Methyl-1,2,3,6-tetrahydropyridin-4-yl)-5-(trifluoromethyl)benzenamine

HRID 887544노트

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HRID 887544 반응식
CC1(C)COB([C:8]2[CH:9]=[C:10]([NH2:18])[CH:11]=[C:12]([C:14]([F:17])([F:16])[F:15])[CH:13]=2)OC1.[CH3:20][N:21]1[CH2:26][CH:25]=[C:24](OS(C(F)(F)F)(=O)=O)[CH2:23][CH2:22]1.C([O-])([O-])=O.[Na+].[Na+]>CCOCC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:20][N:21]1[CH2:22][CH:23]=[C:24]([C:8]2[CH:9]=[C:10]([NH2:18])[CH:11]=[C:12]([C:14]([F:15])([F:16])[F:17])[CH:13]=2)[CH2:25][CH2:26]1

참가 물질

6

반응물 3

HCID 10340Sodium CarbonateHCID 113795771-Methyl-1,2,3,6-tetrahydropyridin-4-yl trifluoromethanesulfonateHCID 219596073-(5,5-Dimethyl-[1,3,2]dioxaborinan-2-yl)-5-trifluoromethyl-phenylamine

생성물 1

HCID 219596433-(1-Methyl-1,2,3,6-tetrahydropyridin-4-yl)-5-(trifluoromethyl)benzenamine

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 3283Diethyl Ether용매

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온도
80 °C

실험 절차

3-(5,5-Dimethyl-[1,3,2]dioxaborinan-2-yl)-5-trifluoromethyl-phenylamine (8.8 g, 0.032 mol) was added to trifluoro-methanesulfonic acid 1-methyl-1,2,3,6-tetrahydro-pyridin-4-yl ester (7.91 g, 0.032 mol) and 2N Na2CO3 aqueous solution (25 mL) was bubbled through N2 for 5 min. Pd(PPh3)4 (3.7 g, 3.2 mmol) was added and the reaction was heated to 80° C. for 16 h. The reaction was cooled to RT and diluted with Et2O (100 mL). The mixture was filtered through Celite® and the filtrate was washed with NaHCO3 aqueous solution (25 ml) followed by brine (25 mL). The organic phase was dried over Na2SO4 and concentrated in vacuo. The desired compound was isolated by passing through silica gel column chromatography (EtOAc, then (2M NH3) in MeOH/EtOAc) to provide a yellow oil.

후처리

  1. customwas bubbled through N2 for 5 min
  2. temperatureThe reaction was cooled to RT
  3. filtrationThe mixture was filtered through Celite®
  4. washthe filtrate was washed with NaHCO3 aqueous solution (25 ml)
  5. dry with materialThe organic phase was dried over Na2SO4
  6. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-6b84a97c946d40d2820ffee94dadc400
출처 데이터셋
uspto-grants-2012_08
특허 번호
US08247430B2

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