4-Methoxycarbonylphenylboronic acid → 4-Thiazol-4-yl-benzoic acid methyl ester

HRID 646404ノート

反応式

HRID 646404 の反応式
Br[C:2]1[N:3]=[CH:4][S:5][CH:6]=1.[CH3:7][O:8][C:9]([C:11]1[CH:16]=[CH:15][C:14](B(O)O)=[CH:13][CH:12]=1)=[O:10]>O1CCOCC1.C([O-])([O-])=O.[Na+].[Na+].[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:7][O:8][C:9](=[O:10])[C:11]1[CH:16]=[CH:15][C:14]([C:2]2[N:3]=[CH:4][S:5][CH:6]=2)=[CH:13][CH:12]=1

参加物

6

反応物 2

HCID 27343694-Methoxycarbonylphenylboronic acidHCID 27632184-Bromothiazole

生成物 1

HCID 592646784-Thiazol-4-yl-benzoic acid methyl ester収率 45%

試薬・触媒・溶媒 3

HCID 11979704Tetrakis(triphenylphosphine)palladium触媒HCID 10340Sodium Carbonate溶媒HCID 312751,4-Dioxane溶媒

実験手順

A suspension of 4-bromothiazole (1.13 g, 6.89 mmol), 4-methoxycarbonylphenylboronic acid (1.85 g, 10.3 mmol) and Tetrakis (triphenylphosphine) palladium (0) (0.35 g, 0.30 mmol) in dioxane (45 mL) and 2M Na2CO3 (17.2 mL) is heated to reflux for 18 h. The reaction is allowed to cool and filtered. The filtrate is evaporated in vacuo, and the residue is dissolved in ethyl acetate and washed with water (2×) and brine (2×). The combined organic layers are dried over Na2SO4, and concentrated in vacuo. The crude material is purified by flash chromatography (100% hexanes-40% ethyl acetate/hexanes) to give 4-thiazol-4-yl-benzoic acid methyl ester as a white solid (0.68 g, 45%) MS (ES+) 220.2

後処理

  1. temperatureis heated
  2. temperatureto reflux for 18 h
  3. temperatureto cool
  4. filtrationfiltered
  5. customThe filtrate is evaporated in vacuo
  6. dissolutionthe residue is dissolved in ethyl acetate
  7. washwashed with water (2×) and brine (2×)
  8. dry with materialThe combined organic layers are dried over Na2SO4
  9. concentrationconcentrated in vacuo
  10. customThe crude material is purified by flash chromatography (100% hexanes-40% ethyl acetate/hexanes)

出典と根拠

ORDレコード
ord-ffe38e277e3c41359e313f7110b4b9a9
出典データセット
uspto-grants-2010_04
特許番号
US07705025B2

反応ノート

読み込み中…