Potassium Carbonate → (S)-6-(2-methylpyrrolidin-1-yl)-3-nitro-2-(trifluoromethyl)pyridine

HRID 1805163ノート

反応式

HRID 1805163 の反応式
Br[C:2]1[N:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[C:5]([N+:12]([O-:14])=[O:13])=[CH:4][CH:3]=1.S(C1C=CC(C)=CC=1)(O)(=O)=O.[CH3:26][C@H:27]1[CH2:31][CH2:30][CH2:29][NH:28]1.C([O-])([O-])=O.[K+].[K+]>O>[CH3:26][C@H:27]1[CH2:31][CH2:30][CH2:29][N:28]1[C:2]1[N:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[C:5]([N+:12]([O-:14])=[O:13])=[CH:4][CH:3]=1

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 44118660(S)-2-Methylpyrrolidine 4-methylbenzenesulfonateHCID 593162396-Bromo-3-nitro-2-(trifluoromethyl)pyridine

生成物 1

HCID 59410063(S)-6-(2-methylpyrrolidin-1-yl)-3-nitro-2-(trifluoromethyl)pyridine収率 88%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
140 °C

実験手順

A suspension of 6-bromo-3-nitro-2-(trifluoromethyl)pyridine (400 mg, 1.5 mmoL), (S)-2-methylpyrrolidine tosylate salt (381 mg, 1.5 mmoL) and K2CO3 (620 mg, 4.5 mmoL) in H2O (4 mL) was heated at 140° C. under microwave irradiation for 30 minutes. The solution was extracted with EtOAc (50 mL×3) and the combined organic layer was washed with brine, dried over anhydrous Na2SO4 and purified by silica gel column chromatography to afford (S)-6-(2-methylpyrrolidin-1-yl)-3-nitro-2-(trifluoromethyl)pyridine (350 mg, 88% yield). 1H NMR (400 MHz, CDCl3) δ 8.14 (d, J=9.2 Hz, 1H), 6.44 (d, J=8.4 Hz, 1H), 4.55-4.42 (m, 1H), 4.02-3.30 (m, 2H), 2.30-2.00 (m, 3H), 1.81 (brs, 1H), 1.27 (d, J=6.4 Hz, 3H).

後処理

  1. extractionThe solution was extracted with EtOAc (50 mL×3)
  2. washthe combined organic layer was washed with brine
  3. dry with materialdried over anhydrous Na2SO4
  4. custompurified by silica gel column chromatography

出典と根拠

ORDレコード
ord-19cca712e0b3463089f49ac006e20aa7
出典データセット
uspto-grants-2013_01
特許番号
US08354427B2

反応ノート

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