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

HRID 2117683

Reaction equation

HRID 2117683 reaction equation
[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

Participants

8

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 4

HCID 11776TriphenylphosphineCatalystHCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-643509fcb6bb418b9af9da1c208103c7
Source dataset
uspto-grants-2008_10
Patent number
US07442719B2

Linked notes

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