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Sodium Carbonate → Propane-2-sulfonic acid {2-[4'-(2-hydroxy-ethyl)-biphenyl-4-yl]-thiophen-3-yl}amide

HRID 746781
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HRID 746781 반응식
CC1(C)C(C)(C)OB([C:9]2[CH:14]=[CH:13][C:12]([C:15]3[S:16][CH:17]=[CH:18][C:19]=3[NH:20][S:21]([CH:24]([CH3:26])[CH3:25])(=[O:23])=[O:22])=[CH:11][CH:10]=2)O1.C(=O)([O-])[O-].[Na+].[Na+].Br[C:35]1[CH:40]=[CH:39][C:38]([CH2:41][CH2:42][OH:43])=[CH:37][CH:36]=1>COCCOC.CCO>[OH:43][CH2:42][CH2:41][C:38]1[CH:39]=[CH:40][C:35]([C:9]2[CH:10]=[CH:11][C:12]([C:15]3[S:16][CH:17]=[CH:18][C:19]=3[NH:20][S:21]([CH:24]([CH3:25])[CH3:26])(=[O:22])=[O:23])=[CH:13][CH:14]=2)=[CH:36][CH:37]=1
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참가 물질

6

반응물 3

HCID 10340Sodium CarbonateHCID 728512-(4-Bromophenyl)ethanolHCID 59747992Propane-2-sulfonic acid {2-[4-(4,4,5,5-tetramethyl-[1,3,2] dioxaborolan-2-yl)-phenyl]-thiophen-3-yl}-amide

생성물 1

HCID 90690755Propane-2-sulfonic acid {2-[4'-(2-hydroxy-ethyl)-biphenyl-4-yl]-thiophen-3-yl}amide

시약·촉매·용매 2

HCID 702Ethanol용매
HCID 8071
1,2-Dimethoxyethane
용매

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온도
92.5 °C

실험 절차

Mix propane-2-sulfonic acid{2-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-thiophen-3-yl}-amide (0.10 g), 0.1 equiv of tetrakis triphenylphosphine palladium (0), 2 equiv of 2M sodium carbonate aqueous solution in DME (2 mL) and EtOH(1 mL) and warm to 90-95° C. After warming two min, add 2-(4-bromo-phenyl)-ethanol (1.3 equiv) and stir at that temperature for 1.5 h. Evaporate solvents over Celite® and purify by silica gel Strata® cartridges eluting with hexanes-EtOAc gradient to give 0.041 g of the title compound. MS (ES+) (m/z): 402 (M+1).

후처리

  1. temperatureAfter warming two min
  2. customEvaporate solvents over Celite® and purify by silica gel Strata® cartridges
  3. washeluting with hexanes-EtOAc gradient

출처 및 근거

ORD 기록
ord-97b0e8c9c2a14cf698b75686a82e6caa
출처 데이터셋
uspto-grants-2008_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07393868B2

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