Sodium Carbonate → 6-Nitro-4'-[3-(propane-2-sulfonylamino)-thiophen-2-yl]-biphenyl-2-carboxylic acid methyl ester

HRID 746782

반응식

HRID 746782 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.[CH3:28][O:29][C:30](=[O:41])[C:31]1[CH:36]=[CH:35][CH:34]=[C:33]([N+:37]([O-:39])=[O:38])[C:32]=1Br.C([O-])([O-])=O.[Na+].[Na+].O1CCOCC1>C(OCC)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:28][O:29][C:30]([C:31]1[C:32]([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)=[C:33]([N+:37]([O-:39])=[O:38])[CH:34]=[CH:35][CH:36]=1)=[O:41]

참가 물질

7

반응물 4

HCID 10340Sodium CarbonateHCID 312751,4-DioxaneHCID 79263Methyl 2-bromo-3-nitrobenzoateHCID 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 692549916-Nitro-4'-[3-(propane-2-sulfonylamino)-thiophen-2-yl]-biphenyl-2-carboxylic acid methyl ester수율 36.2%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 3283Diethyl Ether용매

실험 절차

Heat the mixture of propane-2-sulfonic acid {2-[4-{4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-thiophen-3-yl}-amide(662 mg, 1.65 mmol), 2-bromo-3-nitro-benzoic acid methyl ester (390 mg, 1.5 mmol), Na2CO3(2M, 2.2 mL, 4.5 mmol) and Pd(PPh3)4 (260 mg, 0.26 mmol) and 15 ml of 1,4 dioxane under N2 to 80° C. overnight. After cooling to room temperature, dilute with diethyl ether (200 mL). Wash with water, saturated aq. sodium chloride, and dry over MgSO4. Remove solvent and purify by flash chromatography (Silica gel-hexane/EtOAc) to provide 6-nitro-4′-[3-(propane-2-sulfonylamino)-thiophen-2-yl]-biphenyl-2-carboxylic acid methyl ester (250 mg). MS (m/e): 478.7(M+1).

후처리

  1. temperatureHeat
  2. washWash with water, saturated aq. sodium chloride
  3. dry with materialdry over MgSO4
  4. customRemove solvent and purify by flash chromatography (Silica gel-hexane/EtOAc)

출처 및 근거

ORD 기록
ord-b1cb70f6a81f4af7b8d8ee689862c7ff
출처 데이터셋
uspto-grants-2008_07
특허 번호
US07393868B2

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