Water → HCID 86661726、化合物

HRID 1020817ノート

反応式

HRID 1020817 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

HCID 86661726HCID 86661726、化合物収率 8%

試薬・触媒・溶媒 2

HCID 8857Ethyl Acetate溶媒HCID 18463208dimethoxyethane N,N-dimethylformamide溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-47d9e8230fb6496c9f86d1d1c4697dbb
出典データセット
uspto-grants-2014_05
特許番号
US08716478B2

反応ノート

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