Water → tert-Butyl (2-(5-(4-(4-chlorophenoxy)piperidine-1-carbonyl)-1H-indol-1-yl)ethyl)carbamate

HRID 2170862노트

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HRID 2170862 반응식
[Cl:1][C:2]1[CH:25]=[CH:24][C:5]([O:6][CH:7]2[CH2:12][CH2:11][N:10]([C:13]([C:15]3[CH:16]=[C:17]4[C:21](=[CH:22][CH:23]=3)[NH:20][CH:19]=[CH:18]4)=[O:14])[CH2:9][CH2:8]2)=[CH:4][CH:3]=1.[H-].[Na+].Br[CH2:29][CH2:30][NH:31][C:32](=[O:38])[O:33][C:34]([CH3:37])([CH3:36])[CH3:35].O>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][CH:7]2[CH2:12][CH2:11][N:10]([C:13]([C:15]3[CH:16]=[C:17]4[C:21](=[CH:22][CH:23]=3)[N:20]([CH2:29][CH2:30][NH:31][C:32](=[O:38])[O:33][C:34]([CH3:37])([CH3:36])[CH3:35])[CH:19]=[CH:18]4)=[O:14])[CH2:9][CH2:8]2)=[CH:24][CH:25]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 24758Sodium hydrideHCID 4103526tert-Butyl N-(2-bromoethyl)carbamateHCID 67168639HCID 67168639, 화합물

생성물 1

HCID 86670543tert-Butyl (2-(5-(4-(4-chlorophenoxy)piperidine-1-carbonyl)-1H-indol-1-yl)ethyl)carbamate수율 99%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
70 °C

실험 절차

To a stirred solution of (4-(4-chlorophenoxy)piperidin-1-yl)(1H-indol-5-yl)methanone (80 mg, 0.23 mmol, Step-1 of Example 353) and sodium hydride (60% in oil, 27 mg, 1.13 mmol) in N,N-dimethylformamide (5 mL) was added tert-butyl (2-bromoethyl)carbamate (76 mg, 0.34 mmol) at room temperature. Then the mixture was stirred at 70° C. for 3 hours. The mixture was poured into water (30 mL) and extracted with ethyl acetate (30 mL). The organic layer was washed with water (30 mL), and dried over sodium sulfate. After removal of the solvent, the residue was purified by silica-gel column chromatography (eluting with n-hexane/ethyl acetate=2/1) to give 112 mg (>99% yield) of the title compound as brown oil.

후처리

  1. extractionextracted with ethyl acetate (30 mL)
  2. washThe organic layer was washed with water (30 mL)
  3. dry with materialdried over sodium sulfate
  4. customAfter removal of the solvent
  5. customthe residue was purified by silica-gel column chromatography (eluting with n-hexane/ethyl acetate=2/1)

출처 및 근거

ORD 기록
ord-d96ba931e51a4d47af6ba7d08527f8c1
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09051296B2

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