Dichloromethane → {4-[2-(Pyrid-3-yl)ethenyl]-2-phenylbenzoyl}methionine methyl ester

HRID 2121187ノート

反応式

HRID 2121187 の反応式
[CH3:1][O:2][C:3](=[O:25])[C@H:4]([CH2:21][CH2:22][S:23][CH3:24])[NH:5][C:6](=[O:20])[C:7]1[CH:12]=[CH:11][C:10](I)=[CH:9][C:8]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[CH:26]([C:28]1[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=1)=[CH2:27].C(N(CC)CC)C.ClCCl>CN(C=O)C.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH3:1][O:2][C:3](=[O:25])[C@H:4]([CH2:21][CH2:22][S:23][CH3:24])[NH:5][C:6](=[O:20])[C:7]1[CH:12]=[CH:11][C:10]([CH:27]=[CH:26][C:28]2[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=2)=[CH:9][C:8]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

参加物

7

反応物 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 142723-VinylpyridineHCID 53801632(4-Iodo-2-phenylbenzoyl)methionine methyl ester

生成物 1

HCID 54096885{4-[2-(Pyrid-3-yl)ethenyl]-2-phenylbenzoyl}methionine methyl ester収率 58.5%

試薬・触媒・溶媒 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

A mixture of the (4-iodo-2-phenylbenzoyl)methionine methyl ester prepared in Example 210D (655 mg, 1.40 mmol), the vinylpyridine prepared in Example 210E (221 mg, 1.5 mmol), triethylamine (0.29 mL, 2.10 mmol), [1,1′-bis(diphenylphosphino)ferrocene]palladium(II) chloride, complexed to dichloromethane (1:1) (114 mg, 0.14 mmol) in DMF (2 mL) was degassed with nitrogen, and heated at 100° C. for 14 hours. The reaction mixture was diluted with ether (100 mL), washed with water and brine, dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo. The residue was purified by column chromatography (ethyl acetate) to give {4-[2-(pyrid-3-yl)ethenyl]-2-phenylbenzoyl}methionine methyl ester (366 mg, 56%). 1H NMR (300 MHz, CDCl3) δ 8.75 (d, 1H), 8.51 (dd, 1H), 7.85 (dt, 1H), 7.76 (d, 1H), 7.59 (dd, 1H), 7.48 (dd, 1H), 7.44 (m, 5H), 7.31 (dd, 1H), 7.22 (d, 1H), 7.16 (d, 1H), 5.94 (br d, 1H), 4.69 (m, 1H), 3.68 (s, 3H), 2.08 (m, 2H), 2.02 (s, 3H), 1.93 (m, 1H), 1.76 (m, 1H). MS (APCI+) m/e 447 (M+H)+.

後処理

  1. customwas degassed with nitrogen
  2. additionThe reaction mixture was diluted with ether (100 mL)
  3. washwashed with water and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by column chromatography (ethyl acetate)

出典と根拠

ORDレコード
ord-9aec97e08c3b49d79de42414ef7fd3a5
出典データセット
uspto-grants-2004_02
特許番号
US06693123B2

反応ノート

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