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

HRID 551986ノート

反応式

HRID 551986 の反応式
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]

参加物

8

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 4

HCID 178418476HCID 178418476、化合物触媒HCID 178505378HCID 178505378、化合物触媒HCID 3283Diethyl Ether溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
120 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-1c7390b978cf47a4b64fed4d53339403
出典データセット
uspto-grants-2011_05
特許番号
US07947851B2

反応ノート

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