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

HRID 646254ノート

反応式

HRID 646254 の反応式
[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]

参加物

8

反応物 4

HCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 57435852HCID 57435852、化合物HCID 597727121-Ethyl-4-iodo-2-methanesulfonyl-1H-pyrrole

生成物 1

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

試薬・触媒・溶媒 3

HCID 178418476HCID 178418476、化合物触媒HCID 6228Dimethylformamide溶媒2 回HCID 8857Ethyl Acetate溶媒

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-5b5c9823f0ed4ba6bf0bfe61e6e36d94
出典データセット
uspto-grants-2010_04
特許番号
US07705030B2

反応ノート

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