Triethylamine → 4-(3-Bromo-4-fluoro-phenylethynyl)-1-ethyl-2-methanesulfonyl-1H-pyrrole

HRID 2220471Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2220471
[CH2:1]([N:3]1[CH:7]=[C:6](I)[CH:5]=[C:4]1[S:9]([CH3:12])(=[O:11])=[O:10])[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N(CC)CC)C.[Br:39][C:40]1[CH:45]=[C:44]([C:46]#[CH:47])[CH:43]=[CH:42][C:41]=1[F:48]>CN(C=O)C.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.CCOC(C)=O>[Br:39][C:40]1[CH:45]=[C:44]([C:46]#[C:47][C:6]2[CH:5]=[C:4]([S:9]([CH3:12])(=[O:11])=[O:10])[N:3]([CH2:1][CH3:2])[CH:7]=2)[CH:43]=[CH:42][C:41]=1[F:48]

Komponenten

8

Edukt 4

HCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 57435852HCID 57435852, VerbindungHCID 597727121-Ethyl-4-iodo-2-methanesulfonyl-1H-pyrrole

Produkt 1

HCID 597727414-(3-Bromo-4-fluoro-phenylethynyl)-1-ethyl-2-methanesulfonyl-1H-pyrroleAusbeute 2 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418476HCID 178418476, VerbindungKatalysatorHCID 6228DimethylformamideLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of 1-ethyl-4-iodo-2-methanesulfonyl-1H-pyrrole (0.28 g, 0.94 mmol) in DMF was treated with dichlorobis(triphenylphosphine)-palladium(II) (0.033 g, 0.05 mmol), triphenylphosphine (0.0054 g, 0.028 mmol) and triethylamine (0.68 mL, 4.9 mmol), treated dropwise with a solution of 2-bromo-4-ethynyl-1-fluorobenzene (0.28 g, 1.4 mmol) in DMF, stirred at room temperature for 18 h, poured into EtOAc and washed sequentially with water and brine. The organic phase is separated, dried (Na2SO4) and concentrated in vacuo. Chromatography of the resultant residue (silica gel, 2%-20% EtOAC-hexanes as eluent) yielded an oil; 1H NMR (400 MHz, CDCl3) δ: 1.50 (t, 3H, J=7.3 Hz), 3.12 (s, 3H), 4.28 (q, 2H, J=7.3 Hz), 7.01 (d, 1H, J=1.8 Hz), 7.07 (t, 1H, J=8.5 Hz), 7.12 (d, 1H, J=1.8 Hz), 7.37 (m, 1H), 7.66 (dd, 1H, J=2.1, 6.6 Hz).

Aufarbeitung

  1. washwashed sequentially with water and brine
  2. customThe organic phase is separated
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-7d8a53d8edb249ea8a596f743d8fe395
Quelldatensatz
uspto-grants-2008_08
Patentnummer
US07417047B2

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