Water → HCID 86661726, 화합물

HRID 1020817노트

반응식

HRID 1020817 반응식
[F:1][C:2]([F:8])([F:7])[O:3][CH2:4][CH2:5][OH:6].Cl[C:10]1[N:18]=[C:17]([Cl:19])[C:16]([Cl:20])=[CH:15][C:11]=1[C:12]([NH2:14])=[O:13].C(O[K])(C)(C)C.O>CN(C=O)C.COCCOC.CCOC(C)=O>[Cl:20][C:16]1[C:17]([Cl:19])=[N:18][C:10]([O:6][CH2:5][CH2:4][O:3][C:2]([F:8])([F:7])[F:1])=[C:11]([CH:15]=1)[C:12]([NH2:14])=[O:13]

참가 물질

7

반응물 4

HCID 962WaterHCID 179516872-(Trifluoromethoxy)ethan-1-olHCID 537509302,5,6-Trichloropyridine-3-carboxamideHCID 178418922HCID 178418922, 화합물

생성물 1

HCID 86661726HCID 86661726, 화합물수율 8%

시약·촉매·용매 2

HCID 8857Ethyl Acetate용매HCID 18463208dimethoxyethane N,N-dimethylformamide용매

실험 절차

To a mixture of compound 2-(trifluoromethoxy)ethanol (9.5 mmol) in DMF/DME (20/50 mL) was added 2,5,6-trichloronicotinamide (2.1 g, 9.5 mmol) and tert-BuOK (1.30 g, 11.4 mmol) and the reaction mixture was stirred at room temperature overnight. The mixture was poured into 100 mL of cold water, diluted with 100 mL of EtOAc, the organic layer was separated and the aqueous phase was further extracted twice with EtOAc, the combined organic layers were washed with brine twice, dried over Na2SO4 and concentrated, the residue was purified by silica gel chromatography (Petroleum ether:EtOAc=1:0 to 5:1) to give 5,6-dichloro-2-(2-(trifluoromethoxy)ethoxy)nicotinamide (0.24 g, 8%). 1H-NMR (400 MHz, DMSO-d6) δ (ppm) 8.31 (s, 1H), 7.97 (s, 1H), 7.59 (s, 1H), 4.62 (t, 2H, J=4.0 Hz), 4.51 (t, 2H, J=4.0 Hz).

후처리

  1. customthe organic layer was separated
  2. extractionthe aqueous phase was further extracted twice with EtOAc
  3. washthe combined organic layers were washed with brine twice
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customthe residue was purified by silica gel chromatography (Petroleum ether:EtOAc=1:0 to 5:1)

출처 및 근거

ORD 기록
ord-47d9e8230fb6496c9f86d1d1c4697dbb
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08716478B2

반응 노트

불러오는 중…