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2-Bromopropiophenone → 2-[4-(4-Cyclopentyl-piperazine-1-carbonyl)-indol-1-yl]-1-phenyl-propan-1-one

HRID 225438
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반응식

HRID 225438 반응식
[CH:1]1([N:6]2[CH2:11][CH2:10][N:9]([C:12]([C:14]3[CH:22]=[CH:21][CH:20]=[C:19]4[C:15]=3[CH:16]=[CH:17][NH:18]4)=[O:13])[CH2:8][CH2:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.Br[CH:24]([CH3:33])[C:25]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:26].CC(C)([O-])C.[Na+]>C1COCC1>[CH:1]1([N:6]2[CH2:7][CH2:8][N:9]([C:12]([C:14]3[CH:22]=[CH:21][CH:20]=[C:19]4[C:15]=3[CH:16]=[CH:17][N:18]4[CH:24]([CH3:33])[C:25]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[O:26])=[O:13])[CH2:10][CH2:11]2)[CH2:5][CH2:4][CH2:3][CH2:2]1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 164522-BromopropiophenoneHCID 23676156Sodium t-butoxideHCID 57752820(4-cyclopentyl-piperazin-1-yl)-(1H-indol-4-yl)-methanone2회

생성물 1

HCID 249912962-[4-(4-Cyclopentyl-piperazine-1-carbonyl)-indol-1-yl]-1-phenyl-propan-1-one수율 6.1%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A mixture of 29.8 mg (0.1 mmol) (4-cyclopentyl-piperazin-1-yl)-(1H-indol-4-yl)-methanone (intermediate 2), 32 mg (0.15 mmol) 2-bromo-1-phenyl-propan-1-one (commercially available) and 28.8 mg (0.3 mmol) sodium-tert-butoxide in 2 mL THF was shaken at room temperature for 16 h. After evaporation to dryness the residue was dissolved in methanol/DMF and subjected to purification by preparative HPLC on reversed phase eluting with a gradient formed from acetonitrile/water/NEt3. The combined product fractions were evaporated to yield 2.6 mg of the title compound. MS (m/e): 430.5 (MH+).

후처리

  1. customAfter evaporation to dryness the residue
  2. dissolutionwas dissolved in methanol/DMF
  3. customsubjected to purification by preparative HPLC on reversed phase
  4. washeluting with a gradient
  5. customformed from acetonitrile/water/NEt3
  6. customThe combined product fractions were evaporated

출처 및 근거

ORD 기록
ord-9bff5dfb292542c1991d5bbb57294384
출처 데이터셋
uspto-grants-2009_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07557108B2

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