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[(4-Iodophenyl)sulfonyl]-2-pyridylamine → Methyl 2-hydroxy-5-[[4-[(2-pyridinylamino)sulfonyl]phenyl]ethynyl]benzoate

HRID 1653890
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HRID 1653890 반응식
I[C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[C:18]([C:20]1[CH:21]=[CH:22][C:23]([OH:30])=[C:24]([CH:29]=1)[C:25]([O:27][CH3:28])=[O:26])#[CH:19]>C(N(CC)CC)C.O1CCCC1.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.[Cu]I>[OH:30][C:23]1[CH:22]=[CH:21][C:20]([C:18]#[C:19][C:2]2[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=3)(=[O:10])=[O:9])=[CH:4][CH:3]=2)=[CH:29][C:24]=1[C:25]([O:27][CH3:28])=[O:26]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 2

HCID 1143526[(4-Iodophenyl)sulfonyl]-2-pyridylamineHCID 14172485Methyl 5-ethynyl-2-hydroxybenzoate

생성물 1

HCID 19423375Methyl 2-hydroxy-5-[[4-[(2-pyridinylamino)sulfonyl]phenyl]ethynyl]benzoate

시약·촉매·용매 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178418476HCID 178418476, 화합물
촉매
HCID 8028Tetrahydrofuran용매
HCID 8471Triethylamine용매

반응 조건

온도
60 °C

실험 절차

4-Iodo-N-(2-pyridinyl)benzenesulfonamide (35 g, 97 mmol) was dissolved in a mixture of triethylamine and tetrahydrofuran (750+750 ml). The mixture was deaerated with nitrogen and dichlorobis(triphenylphosphine)palladium (1.2 g, 1.7 mmol) and copper(I) iodide (0.6 g, 3.4 mmol) were added. Finally methyl 5-ethynyl-2-hydroxybenzoate (23 g, 130 mmol) was added. The mixture was heated to 60° C. for 4 h, evaporated to dryness. The residue was dissolved in chloroform (1000 ml) and washed with water (3×200 ml) and dried with MgSO4. The solvent was evaporated in vacuo. Yield 31 g (77% ). The product can be purified by flash-chromatography on silica with chloroform as the eluent.

후처리

  1. additionwere added
  2. customevaporated to dryness
  3. dissolutionThe residue was dissolved in chloroform (1000 ml)
  4. washwashed with water (3×200 ml)
  5. dry with materialdried with MgSO4
  6. customThe solvent was evaporated in vacuo
  7. customThe product can be purified by flash-chromatography on silica with chloroform as the eluent

출처 및 근거

ORD 기록
ord-aa5b3e4a77234ff6b29b1d30e6734505
출처 데이터셋
uspto-grants-1995_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05403930

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