2-(Tributylstannyl)pyridine → 3-[4-(4-Acetyl-3-hydroxy-2-pyridin-2-yl-phenoxymethyl)-benzyl]-benzoic acid methyl ester

HRID 1818570ノート

反応式

HRID 1818570 の反応式
[CH3:1][O:2][C:3](=[O:30])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([CH2:17][O:18][C:19]3[CH:24]=[CH:23][C:22]([C:25](=[O:27])[CH3:26])=[C:21]([OH:28])[C:20]=3I)=[CH:13][CH:12]=2)[CH:5]=1.C([Sn](CCCC)(CCCC)[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][N:37]=1)CCC>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:1][O:2][C:3](=[O:30])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([CH2:17][O:18][C:19]3[CH:24]=[CH:23][C:22]([C:25](=[O:27])[CH3:26])=[C:21]([OH:28])[C:20]=3[C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][N:37]=3)=[CH:13][CH:12]=2)[CH:5]=1

参加物

5

反応物 2

HCID 6077842-(Tributylstannyl)pyridineHCID 666995233-[4-(4-Acetyl-3-hydroxy-2-iodo-phenoxymethyl)-benzyl]-benzoic acid methyl ester

生成物 1

HCID 1360880293-[4-(4-Acetyl-3-hydroxy-2-pyridin-2-yl-phenoxymethyl)-benzyl]-benzoic acid methyl ester収率 60.9%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 1140Toluene溶媒

反応条件

温度
100 °C

実験手順

A mixture of 3-[4-(4-acetyl-3-hydroxy-2-iodo-phenoxymethyl)-benzyl]-benzoic acid methyl ester (417 mg, 0.808 mmol), 2-tributylstannanyl-pyridine (1.72 g, 4.67 mmol), and tetrakis(triphenylphosphine)palladium(0) (111 mg, 0.096 mmol) in toluene (19 mL) is thoroughly degassed, placed under nitrogen and heated at 100° C. for 16 hours. After cooling to room temperature, the reaction mixture is concentrated in vacuo. The residue thus obtained is purified by flash chromatography (20% to 40% ethylacetate in hexanes) to give 230 mg of the title compound as a yellow oil: MS (m/z): 468 (M+1); 1H NMR (CDCl3) δ 8.74 (m, 1H), 7.87 (m, 2H), 7.78 (m, 2H), 7.56 (d, J=8.0 Hz, 1H), 7.36-7.27 (m, 3H), 7.17 (d, J=8.0 Hz, 2H), 7.11 (d, J=8.0 Hz, 2H), 6.60 (d, J=9.0 Hz, 1H), 5.14 (s, 2H), 3.99 (s, 2H), 3.89 (s, 3H), 2.61 (s, 3H).

後処理

  1. customis thoroughly degassed
  2. temperatureAfter cooling to room temperature
  3. concentrationthe reaction mixture is concentrated in vacuo
  4. customThe residue thus obtained
  5. customis purified by flash chromatography (20% to 40% ethylacetate in hexanes)

出典と根拠

ORDレコード
ord-a8139e0a0b8c4f9da14f621528a912ab
出典データセット
uspto-grants-2009_10
特許番号
US07598423B2

反応ノート

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