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

HRID 2117683

반응식

HRID 2117683 반응식
[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

참가 물질

8

반응물 3

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

생성물 1

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

시약·촉매·용매 4

HCID 11776Triphenylphosphine촉매HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178418476HCID 178418476, 화합물촉매HCID 8028Tetrahydrofuran용매2회

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-643509fcb6bb418b9af9da1c208103c7
출처 데이터셋
uspto-grants-2008_10
특허 번호
US07442719B2

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