4-iodo-N-(3-methyl-2-pyridinyl)benzenesulfonamide → Ethyl 2-hydroxy-5-[[4-[(3-methyl-2-pyridinylamino)sulfonyl]phenyl]ethynyl]benzoate

HRID 1464163노트

반응식

HRID 1464163 반응식
[C:1]([C:3]1[CH:4]=[CH:5][C:6]([OH:14])=[C:7]([CH:13]=1)[C:8]([O:10][CH2:11][CH3:12])=[O:9])#[CH:2].I[C:16]1[CH:21]=[CH:20][C:19]([S:22]([NH:25][C:26]2[C:31]([CH3:32])=[CH:30][CH:29]=[CH:28][N:27]=2)(=[O:24])=[O:23])=[CH:18][CH:17]=1>O1CCCC1.C(N(CC)CC)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.[Cu]I>[OH:14][C:6]1[CH:5]=[CH:4][C:3]([C:1]#[C:2][C:16]2[CH:21]=[CH:20][C:19]([S:22]([NH:25][C:26]3[C:31]([CH3:32])=[CH:30][CH:29]=[CH:28][N:27]=3)(=[O:24])=[O:23])=[CH:18][CH:17]=2)=[CH:13][C:7]=1[C:8]([O:10][CH2:11][CH3:12])=[O:9]

참가 물질

7

반응물 2

HCID 37926154-iodo-N-(3-methyl-2-pyridinyl)benzenesulfonamideHCID 19423366Ethyl 5-ethynyl-2-hydroxybenzoate

생성물 1

HCID 19423387Ethyl 2-hydroxy-5-[[4-[(3-methyl-2-pyridinylamino)sulfonyl]phenyl]ethynyl]benzoate

시약·촉매·용매 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178418397HCID 178418397, 화합물촉매HCID 8028Tetrahydrofuran용매HCID 8471Triethylamine용매

실험 절차

Tetrakis(triphenylphosphine)palladium (0.29 g, 0.25 mmol) and copper(I)iodide (0.095 g, 0.5 mmol) were, added to a solution of ethyl 5-ethynyl-2-hydroxybenzoate (10.5 g, 55 mmol) and 4-iodo-N-(3-methyl-2-pyridinyl)benzenesulfonamide (18.7 g, 50 mmol) in tetrahydrofuran (75 ml) and triethylamine (75 ml) at 55° C. After 2 h the solid product was collected with filtration and washed with hydrochloric acid (1M). The material was boiled in formic acid (300 ml) for 15 nun. and filtered. Water (200 ml) was added and the product crystallized upon cooling. Yield 17.3 g (79%).

후처리

  1. filtrationAfter 2 h the solid product was collected with filtration
  2. washwashed with hydrochloric acid (1M)
  3. filtrationand filtered
  4. additionWater (200 ml) was added
  5. customthe product crystallized
  6. temperatureupon cooling

출처 및 근거

ORD 기록
ord-79c175d99c2743b3868acff9fb4b39ae
출처 데이터셋
uspto-grants-1994_04
특허 번호
US05302718

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