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Sodium Carbonate → 4-[5-(4-Methanesulfonyl-phenyl)-benzofuran-2-yl]-piperidine-1-carboxylic acid tert-butyl ester

HRID 533111
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HRID 533111 반응식
C([O-])([O-])=O.[Na+].[Na+].[C:7]([O:11][C:12]([N:14]1[CH2:19][CH2:18][CH:17]([C:20]2[O:21][C:22]3[CH:28]=[CH:27][C:26](Br)=[CH:25][C:23]=3[CH:24]=2)[CH2:16][CH2:15]1)=[O:13])([CH3:10])([CH3:9])[CH3:8].[CH3:30][S:31]([C:34]1[CH:39]=[CH:38][C:37](B(O)O)=[CH:36][CH:35]=1)(=[O:33])=[O:32]>O1CCOCC1.O>[C:7]([O:11][C:12]([N:14]1[CH2:19][CH2:18][CH:17]([C:20]2[O:21][C:22]3[CH:28]=[CH:27][C:26]([C:37]4[CH:38]=[CH:39][C:34]([S:31]([CH3:30])(=[O:33])=[O:32])=[CH:35][CH:36]=4)=[CH:25][C:23]=3[CH:24]=2)[CH2:16][CH2:15]1)=[O:13])([CH3:10])([CH3:9])[CH3:8]
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참가 물질

5

반응물 3

HCID 10340Sodium CarbonateHCID 27343644-(Methanesulfonyl)phenylboronic acidHCID 86686878HCID 86686878, 화합물

생성물 1

HCID 866868794-[5-(4-Methanesulfonyl-phenyl)-benzofuran-2-yl]-piperidine-1-carboxylic acid tert-butyl ester

시약·촉매·용매 1

HCID 218864351,4-Dioxane--water (1/1)용매

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온도
100 °C

실험 절차

An aqueous Na2CO3 solution (2 M, 0.68 mL) is added to a mixture of 4-(5-bromo-benzofuran-2-yl)-piperidine-1-carboxylic acid tert-butyl ester (2.50 g) and 4-(methanesulfonyl)phenylboronic acid (1.97 g) in a mixture of dioxane/water (60:40). The mixture is sparged with argon for 10 min and PdCl2[1,1′-bis(diphenylphosphino)-ferrocene]*CH2Cl2 complex (500 mg) is added. The resulting mixture is heated to 100° C. for 2 h. After cooling to room temperature, ethyl acetate, brine, and activated charcoal are added. The mixture is filtered and the organic phase is separated, dried over Na2SO4, and the solvent is evaporated. The residue is chromatographed on silica gel (cyclohexane/ethyl acetate 80:20→60:40) to give the title compound. LC (method 1): tR=1.80 min; Mass spectrum (ESI+): m/z=478 [M+Na]+.

후처리

  1. customThe mixture is sparged with argon for 10 min
  2. additionPdCl2[1,1′-bis(diphenylphosphino)-ferrocene]*CH2Cl2 complex (500 mg) is added
  3. temperatureAfter cooling to room temperature
  4. additionethyl acetate, brine, and activated charcoal are added
  5. filtrationThe mixture is filtered
  6. customthe organic phase is separated
  7. dry with materialdried over Na2SO4
  8. customthe solvent is evaporated
  9. customThe residue is chromatographed on silica gel (cyclohexane/ethyl acetate 80:20→60:40)

출처 및 근거

ORD 기록
ord-edc422d760b44037808d4fd0f950866c
출처 데이터셋
uspto-grants-2014_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08853239B2

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