Piperidine → Methyl 2'-fluoro-5'-(methyloxy)-2-(1-piperidinylmethyl)-1,1'-biphenyl-4-carboxylate

HRID 1662461노트

반응식

HRID 1662461 반응식
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Br[CH2:8][C:9]1[CH:14]=[C:13]([C:15]([O:17][CH3:18])=[O:16])[CH:12]=[CH:11][C:10]=1[C:19]1[CH:24]=[C:23]([O:25][CH3:26])[CH:22]=[CH:21][C:20]=1[F:27].C([O-])([O-])=O.[Cs+].[Cs+].CCOC(C)=O>CS(C)=O>[F:27][C:20]1[CH:21]=[CH:22][C:23]([O:25][CH3:26])=[CH:24][C:19]=1[C:10]1[CH:11]=[CH:12][C:13]([C:15]([O:17][CH3:18])=[O:16])=[CH:14][C:9]=1[CH2:8][N:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

참가 물질

6

반응물 4

HCID 8082PiperidineHCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 57705537Methyl 2-(bromomethyl)-2'-fluoro-5'-(methyloxy)-1,1'-biphenyl-4-carboxylate

생성물 1

HCID 57705872Methyl 2'-fluoro-5'-(methyloxy)-2-(1-piperidinylmethyl)-1,1'-biphenyl-4-carboxylate수율 76%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

실험 절차

Piperidine (commercially available from Aldrich) (0.038 g, 0.44 mmol) was added to a solution of 66.63B (0.13 g, 0.37 mmol) in DMSO (3 mL). Cs2CO3 (0.18 g, 0.55 mmol) was then added to the reaction and it was stirred at room temperature for 1 hour. EtOAc (100 mL) was added and the organic phase was washed with water and brine and dried over anhydrous sodium sulfate. After removing solvent, the residue was purified by flash chromatography (silica gel, 1:1 EtOAc/DCM) and gave 66.64A (100 mg) in 76% yield. MS ESI (pos.) m/e: 358 (M+H)+.

후처리

  1. washthe organic phase was washed with water and brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. customAfter removing solvent
  4. customthe residue was purified by flash chromatography (silica gel, 1:1 EtOAc/DCM)

출처 및 근거

ORD 기록
ord-c514047a4600491998ed7489fdaaa0cf
출처 데이터셋
uspto-grants-2011_10
특허 번호
US08030354B2

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