Triethylamine → 1-(3-Fluoro-2-(trifluoromethyl)isonicotinoyl)piperidin-4-one

HRID 1617391ノート

反応式

HRID 1617391 の反応式
[NH:1]1[CH2:6][CH2:5][C:4](=[O:7])[CH2:3][CH2:2]1.[F:8][C:9]1[C:17]([C:18]([F:21])([F:20])[F:19])=[N:16][CH:15]=[CH:14][C:10]=1[C:11](O)=[O:12].F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.C(N(CC)CC)C>CN(C=O)C.CCOC(C)=O>[F:8][C:9]1[C:17]([C:18]([F:21])([F:19])[F:20])=[N:16][CH:15]=[CH:14][C:10]=1[C:11]([N:1]1[CH2:6][CH2:5][C:4](=[O:7])[CH2:3][CH2:2]1)=[O:12]

参加物

7

反応物 4

HCID 8471TriethylamineHCID 337214-PiperidoneHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 265964893-Fluoro-2-(trifluoromethyl)isonicotinic acid

生成物 1

HCID 584313981-(3-Fluoro-2-(trifluoromethyl)isonicotinoyl)piperidin-4-one収率 72.4%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of piperidin-4-one (1 g, 10 mmol) and 3-fluoro-2-(trifluoromethyl)isonicotinic acid (2.32 g, 11.1 mmol) in DMF (20 mL) were added benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (5.62 g, 12.7 mmol) and triethylamine (4.43 mL, 31.8 mmol). The mixture was stirred at room temperature overnight and diluted with EtOAc. The solution was washed with brine, dried with sodium sulfate, filtered and concentrated. Purification on silica gel with 50-100% EtOAc/hexanes gave 2.1 g (70% yield) of the title compound. LC/MS found: 291.2 (M+1)+.

後処理

  1. washThe solution was washed with brine
  2. dry with materialdried with sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification on silica gel with 50-100% EtOAc/hexanes

出典と根拠

ORDレコード
ord-241777ae01e844a589dd21892e000513
出典データセット
uspto-grants-2014_07
特許番号
US08765734B2

反応ノート

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