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

HRID 646254노트

반응식

HRID 646254 반응식
[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]

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 178418476HCID 178418476, 화합물촉매HCID 6228Dimethylformamide용매2회HCID 8857Ethyl Acetate용매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-5b5c9823f0ed4ba6bf0bfe61e6e36d94
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07705030B2

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