Cesium carbonate → Tert-butyl 4-(1-{[6-(trifluoromethyl)pyridin-2-yl]thio}ethyl)piperidine-1-carboxylate

HRID 1873848ノート

反応式

HRID 1873848 の反応式
[SH:1][CH:2]([CH:4]1[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6][CH2:5]1)[CH3:3].Br[C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:27])([F:26])[F:25])[N:19]=1.C([O-])([O-])=O.[Cs+].[Cs+]>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C1(C)C=CC=CC=1>[F:25][C:24]([F:27])([F:26])[C:20]1[N:19]=[C:18]([S:1][CH:2]([CH:4]2[CH2:5][CH2:6][N:7]([C:10]([O:12][C:13]([CH3:15])([CH3:14])[CH3:16])=[O:11])[CH2:8][CH2:9]2)[CH3:3])[CH:23]=[CH:22][CH:21]=1

参加物

6

反応物 3

HCID 10796Cesium carbonateHCID 27829022-Bromo-6-(trifluoromethyl)pyridineHCID 59447341tert-Butyl 4-(1-mercaptoethyl)piperidine-1-carboxylate

生成物 1

HCID 59447422Tert-butyl 4-(1-{[6-(trifluoromethyl)pyridin-2-yl]thio}ethyl)piperidine-1-carboxylate収率 94.2%

試薬・触媒・溶媒 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒HCID 1140Toluene溶媒

反応条件

温度
75 °C

実験手順

To a 16 ml vial was added tert-butyl 4-(1-mercaptoethyl)piperidine-1-carboxylate (500 mg, 2.04 mmol), 2-bromo-6-(trifluoromethyl)pyridine (460 mg, 2.04 mmol), Pd(dppf)Cl2 (42 mg, 0.051 mmol) and Cs2CO3 (996 mg, 3.06 mmol) and 4 ml toluene. The vial was flushed with nitrogen, sealed and heated at 75° C. for 36 hours. After cooling to room temperature, the reaction mixture was diluted with 30 ml ether, and washed with 30 ml water. The organics were dried over sodium sulfate, filtered and concentrated. The residue was purified on silica gel column eluted with 1:9 to 1:4 ethyl acetate/hexane to give 750 mg desired product was light yellow oil.

後処理

  1. customThe vial was flushed with nitrogen
  2. customsealed
  3. temperatureAfter cooling to room temperature
  4. additionthe reaction mixture was diluted with 30 ml ether
  5. washwashed with 30 ml water
  6. dry with materialThe organics were dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified on silica gel column
  10. washeluted with 1:9 to 1:4 ethyl acetate/hexane

出典と根拠

ORDレコード
ord-6959e05b06894ce2ae505021ec0458a0
出典データセット
uspto-grants-2012_11
特許番号
US08304434B2

反応ノート

読み込み中…