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Potassium Carbonate → (+,-) Trans Propane-2-sulfonic Acid [2-(4'-cyano-biphenyl-4-yl)-cyclopentyl]-amide

HRID 989488
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HRID 989488 반응식
I[C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]2[CH2:12][CH2:11][CH2:10][C@H:9]2[NH:13][S:14]([CH:17]([CH3:19])[CH3:18])(=[O:16])=[O:15])=[CH:4][CH:3]=1.[C:20]([C:22]1[CH:27]=[CH:26][C:25](B(O)O)=[CH:24][CH:23]=1)#[N:21].C(=O)([O-])[O-].[K+].[K+]>C(O)CC.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:20]([C:22]1[CH:27]=[CH:26][C:25]([C:2]2[CH:7]=[CH:6][C:5]([C@@H:8]3[CH2:12][CH2:11][CH2:10][C@H:9]3[NH:13][S:14]([CH:17]([CH3:19])[CH3:18])(=[O:16])=[O:15])=[CH:4][CH:3]=2)=[CH:24][CH:23]=1)#[N:21]
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참가 물질

7

반응물 3

HCID 11430Potassium CarbonateHCID 27343264-Cyanophenylboronic acidHCID 11784171(+,-) Trans Propane-2-sulfonic Acid [2-(4-iodo-phenyl)-cyclopentyl]-amide

생성물 1

HCID 12144740(+,-) Trans Propane-2-sulfonic Acid [2-(4'-cyano-biphenyl-4-yl)-cyclopentyl]-amide수율 87.7%

시약·촉매·용매 3

HCID 167845palladium(II) acetate
촉매
HCID 962Water용매
HCID 10311-Propanol용매

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온도
90 °C

실험 절차

(+,−) Trans propane-2-sulfonic acid [2-(4-iodo-phenyl)-cyclopentyl]-amide (375 mg, 0.95 mmol, prepared in example 2) and 4-cyanophenylboronic acid (168 mg, 1.14 mmol) were dissolved in 20 mL of n-propanol and 25 mg (0.18 mmol)of potassium carbonate in 5 mL of water added. A catalytic amount of palladium acetate is added (11 mg) and the mixture refluxed at 90° C. for 7 hours. The reaction is worked up as in preparation 6. The combined organics were dried (Na2SO4), filtered and concentrated in vacuo. Purification by silica chromatography using a Chromatotron® was achieved eluting with 99:1 methylene chloride:methanol to afford 307 mg (87%) of the title compound. The NMR was consistent with the assigned structure.

후처리

  1. customThe reaction is worked up as in preparation 6
  2. dry with materialThe combined organics were dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customPurification by silica chromatography
  6. washwas achieved eluting with 99:1 methylene chloride

출처 및 근거

ORD 기록
ord-8a056dec58dc4e3b8e0282d027f213ff
출처 데이터셋
uspto-grants-2003_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06639107B1

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