Triethylamine → 3-{3-[(7-Bromoheptyl)oxy]prop-1-ynyl}benzenesulfonamide

HRID 2117683

反応式

HRID 2117683 の反応式
[CH2:1]([O:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][Br:12])[C:2]#[CH:3].Br[C:14]1[CH:15]=[C:16]([S:20]([NH2:23])(=[O:22])=[O:21])[CH:17]=[CH:18][CH:19]=1.CCN(CC)CC>C1COCC1.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.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Br:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][O:4][CH2:1][C:2]#[C:3][C:14]1[CH:15]=[C:16]([S:20]([NH2:23])(=[O:22])=[O:21])[CH:17]=[CH:18][CH:19]=1

参加物

8

反応物 3

HCID 8471TriethylamineHCID 27347653-Bromobenzene-1-sulfonamideHCID 218955401-Bromo-7-(prop-2-yn-1-yloxy)heptane

生成物 1

HCID 218953853-{3-[(7-Bromoheptyl)oxy]prop-1-ynyl}benzenesulfonamide収率 46.1%

試薬・触媒・溶媒 4

HCID 11776Triphenylphosphine触媒HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 178418476HCID 178418476、化合物触媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

7-Bromoheptyl prop-2-ynyl ether (55.1 g) in THF (250 ml) was added dropwise over ca 8 h to a stirred mixture of 3-bromobenzenesulfonamide (43.5 g), PdCl2(PPh3)2 (6.48 g), PPh3 (1.45 g), CuI (1.4 g) and Et3N (52 ml) in THF (250 ml) at 55±5° C. under nitrogen then the mixture heated for a further ca 15 hrs. The reaction was cooled, filtered through Celite and the solids washed with THF. The solution was concentrated and the product purified by chromatography on flash silica gel (600 g) eluting with petroleum ether:ethyl acetate (ratios ranging successively from 19:1 to 7:3) to give the title compound (33 g)—LC RT=5.85 min. NMR—300 MHz—δ (CDCl3)—7.95 (1H, t, J 1.5 Hz), 7.78 (1H, dt, J 8, 2 Hz), 7.55 (1H, dt, J 7.75, 2 Hz), 7.40 (1H, t, J 8 Hz), 5.0 (2H, br s), 4.3 (2H, s), 3.4 (2H, t, J 6.5 Hz), 3.35 (2H, t, J 7.25 Hz), 1.75 (2H, m), 1.55 (2H, m), 1.3 (4H, m).

後処理

  1. temperaturethe mixture heated for a further ca 15 hrs
  2. temperatureThe reaction was cooled
  3. filtrationfiltered through Celite
  4. washthe solids washed with THF
  5. concentrationThe solution was concentrated
  6. customthe product purified by chromatography on flash silica gel (600 g)
  7. washeluting with petroleum ether

出典と根拠

ORDレコード
ord-643509fcb6bb418b9af9da1c208103c7
出典データセット
uspto-grants-2008_10
特許番号
US07442719B2

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