Triphenylphosphine → Methyl 5-[({4-[(4-butylphenyl)ethynyl]phenyl}sulfonyl)(hexyl)amino]-2-fluorobenzoate

HRID 551986노트

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HRID 551986 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]([CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[C:12]2[CH:13]=[CH:14][C:15]([F:21])=[C:16]([CH:20]=2)[C:17]([O-:19])=[O:18])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[CH2:28]([C:32]1[CH:37]=[CH:36][C:35]([C:38]#[CH:39])=[CH:34][CH:33]=1)[CH2:29][CH2:30][CH3:31].[C:40]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>CN(C=O)C.CCOCC.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.[I].[Cu]>[CH2:28]([C:32]1[CH:33]=[CH:34][C:35]([C:38]#[C:39][C:2]2[CH:7]=[CH:6][C:5]([S:8]([N:11]([CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[C:12]3[CH:13]=[CH:14][C:15]([F:21])=[C:16]([CH:20]=3)[C:17]([O:19][CH3:40])=[O:18])(=[O:10])=[O:9])=[CH:4][CH:3]=2)=[CH:36][CH:37]=1)[CH2:29][CH2:30][CH3:31]

참가 물질

8

반응물 3

HCID 11776TriphenylphosphineHCID 27751321-Butyl-4-ethynylbenzeneHCID 866265855-[({4-Bromophenyl)sulfonyl](hexyl)amino]-2-fluorobenzoate

생성물 1

HCID 57554500Methyl 5-[({4-[(4-butylphenyl)ethynyl]phenyl}sulfonyl)(hexyl)amino]-2-fluorobenzoate수율 221.5%

시약·촉매·용매 4

HCID 178418476HCID 178418476, 화합물촉매HCID 178505378HCID 178505378, 화합물촉매HCID 3283Diethyl Ether용매HCID 6228Dimethylformamide용매

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온도
120 °C

실험 절차

To a solution of 5-[({4-bromophenyl)sulfonyl](hexyl)amino]-2-fluorobenzoate (400 mg; 0.85 mmol) in DMF (15 mL) under nitrogen were added (p-butylphenyl)acetylene (0.16 mL; 0.93 mmol), bis(triphenylphosphine)palladium chloride (29.7 mg; 0.04 mmol), triphenylphosphine (44.4 mg; 0.17 mmol), copper iodine (8.1 mg; 0.04 mmol) and TEA (0.35 mL; 2.54 mmol). The reaction mixture was stirred under MW at 120° C. for 1500 s. The mixture was diluted with Et2O (75 mL) and the precipitate obtained filtrated off. Filtrate was washed with HCl 1N and with brine. The organic layer was dried over magnesium sulfate and the solvent was removed under reduced pressure. Purification by flash chromatography on silicagel (c-Hex/EtOAc, 95:5 then 90:10) gave 207 mg (44.5%) of the title compound as a yellow cream. HPLC, Rt: 6.17 min (purity=98.5%). LC/MS: M+(ESI): 500.3, 1H NMR (CDCl3) δ: 7.55 (m, 6H), 7.32 (m, 1H), 7.10 (m, 4H), 3.91 (s, 3H), 3.52 (t, J=6.9 Hz, 2H), 2.63 (t, J=7.9 Hz, 2H), 1.30 (m, 12H), 0.95 (m, 3H), 0.85 (t, 3H.

후처리

  1. customthe precipitate obtained
  2. filtrationfiltrated off
  3. washFiltrate was washed with HCl 1N and with brine
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. customthe solvent was removed under reduced pressure
  6. customPurification by flash chromatography on silicagel (c-Hex/EtOAc, 95:5

출처 및 근거

ORD 기록
ord-1c7390b978cf47a4b64fed4d53339403
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07947851B2

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