Sodium Carbonate → HCID 22324115, 화합물

HRID 496100노트

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HRID 496100 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH2:11])(=[O:10])=[O:9])=[C:4]([NH2:12])[CH:3]=1.C(B(CC)[C:16]1[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=1)C.C([O-])([O-])=O.[Na+].[Na+]>COCCOC.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[NH2:12][C:4]1[CH:3]=[C:2]([C:16]2[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=2)[CH:7]=[CH:6][C:5]=1[S:8]([NH2:11])(=[O:10])=[O:9]

참가 물질

6

반응물 3

HCID 10340Sodium CarbonateHCID 6428513-(Diethylboryl)pyridineHCID 1245249554734-81-5

생성물 1

HCID 22324115HCID 22324115, 화합물수율 96.3%

시약·촉매·용매 2

HCID 178418476HCID 178418476, 화합물촉매HCID 80711,2-Dimethoxyethane용매

실험 절차

A mixture of 4-bromo-2-aminobenzenesulfonamide (250 mg, 1.0 mmol), diethyl-3-pyridylborane (225 mg, 1.5 mmol), Pd(PPh3)2Cl2 (35 mg, 5 mol %) in 1,2-dimethoxyethane 30 ml) and Na2CO3 (2M, 3 ml, 6 mmol) were refluxed under N2 for 4 h. The solvents were removed under reduced pressure and the residue was treated with saturated NaHCO3 (20 ml) and extracted with EtOAc (2×40 ml). The organic layer was washed with brine (20 ml), dried (Na2SO4) and the solvent was removed under reduced pressure. The product was purified by flash chromatography on SiO2 using EtOAc:n-hexane (1:1, v/v) as eluent, yielding 240 mg (96%) of 2-amino-4-(3-pyridyl)-benzenesulfonamide as colorless powder. The product was further transformed by Method G (using cyclohexanecarboxaldehyde). M.p. 240-243° C.

후처리

  1. temperaturewere refluxed under N2 for 4 h
  2. customThe solvents were removed under reduced pressure
  3. additionthe residue was treated with saturated NaHCO3 (20 ml)
  4. extractionextracted with EtOAc (2×40 ml)
  5. washThe organic layer was washed with brine (20 ml)
  6. dry with materialdried (Na2SO4)
  7. customthe solvent was removed under reduced pressure
  8. customThe product was purified by flash chromatography on SiO2

출처 및 근거

ORD 기록
ord-090fe85ac1c5452db282e3fb674167eb
출처 데이터셋
uspto-grants-2005_09
특허 번호
US06943159B1

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