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Triethylamine → 4-Bromo-7-(2,2-dimethyl-propionyloxy)-2-phenyl-oxazolo[4,5-c]pyridine-6-carboxylic acid methyl ester

HRID 2388143
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인쇄 미리보기

반응식

HRID 2388143 반응식
[CH3:1][O:2][C:3]([C:5]1[N:10]=[C:9]([Br:11])[C:8]2[N:12]=[C:13]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[O:14][C:7]=2[C:6]=1[OH:21])=[O:4].[CH3:22][C:23]([CH3:28])([CH3:27])[C:24](Cl)=[O:25].C(N(CC)CC)C>CN(C)C1C=CN=CC=1.C(Cl)Cl.C(OCC)(=O)C>[CH3:1][O:2][C:3]([C:5]1[N:10]=[C:9]([Br:11])[C:8]2[N:12]=[C:13]([C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)[O:14][C:7]=2[C:6]=1[O:21][C:24](=[O:25])[C:23]([CH3:28])([CH3:27])[CH3:22])=[O:4]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 3

HCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 866481114-Bromo-7-hydroxy-2-phenyl-oxazolo[4,5-c]pyridine-6-carboxylic acid methyl ester

생성물 1

HCID 866481124-Bromo-7-(2,2-dimethyl-propionyloxy)-2-phenyl-oxazolo[4,5-c]pyridine-6-carboxylic acid methyl ester수율 41.2%

시약·촉매·용매 3

HCID 142844-(Dimethylamino)pyridine
촉매
HCID 6344Dichloromethane용매
HCID 8857Ethyl Acetate용매

실험 절차

A solution of 4-bromo-7-hydroxy-2-phenyl-oxazolo[4,5-c]pyridine-6-carboxylic acid methyl ester (0.1 g, 0.286 mmol; example 3a), trimethylacetyl chloride (42.3 μL, 0.344 mmol), triethylamine (79.7 μL, 0.572 mmol), and 4-(dimethylamino)pyridine (3.5 mg, 0.03 mmol) in methylene chloride (2.5 mL) was stirred at room temperature for 2 hours. The reaction mixture was diluted with ethyl acetate and washed with saturated sodium bicarbonate solution, brine, saturated ammonium chloride solution, and brine. The organic fraction was dried over anhydrous sodium sulfate, and concentrated. The crude product was purified by flash chromatography eluting from silica gel with a gradient of 0-70% ethyl acetate in hexanes to give 51 mg of the title compound as a white solid. MS: (+) m/z 432.8, 434.8 (M+1, 79Br/81Br).

후처리

  1. washwashed with saturated sodium bicarbonate solution, brine, saturated ammonium chloride solution, and brine
  2. dry with materialThe organic fraction was dried over anhydrous sodium sulfate
  3. concentrationconcentrated
  4. customThe crude product was purified by flash chromatography
  5. washeluting from silica gel with a gradient of 0-70% ethyl acetate in hexanes

출처 및 근거

ORD 기록
ord-4b193b5b530b4bdc93e9dedfdb63965f
출처 데이터셋
uspto-grants-2012_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08269008B2

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