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

HRID 646404노트

반응식

HRID 646404 반응식
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

참가 물질

6

반응물 2

HCID 27343694-Methoxycarbonylphenylboronic acidHCID 27632184-Bromothiazole

생성물 1

HCID 592646784-Thiazol-4-yl-benzoic acid methyl ester수율 45%

시약·촉매·용매 3

HCID 11979704Tetrakis(triphenylphosphine)palladium촉매HCID 10340Sodium Carbonate용매HCID 312751,4-Dioxane용매

실험 절차

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

후처리

  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)

출처 및 근거

ORD 기록
ord-ffe38e277e3c41359e313f7110b4b9a9
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07705025B2

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