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

HRID 1653900ノート

反応式

HRID 1653900 の反応式
[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]

参加物

7

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 178418397HCID 178418397、化合物触媒HCID 8028Tetrahydrofuran溶媒HCID 8471Triethylamine溶媒

実験手順

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 (10.5g, 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 min. and filtered. Water (200 ml) was added and the product crystallized upon cooling. Yield 17.3 g (79%). 1H-NMR (Pyridine-d5 as solvent)

後処理

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

出典と根拠

ORDレコード
ord-48bbb154fa4f4a059c3e0969fb7820d4
出典データセット
uspto-grants-1995_04
特許番号
US05403930

反応ノート

読み込み中…