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Potassium Carbonate → 3-(4-Fluoro-phenyl)-7-hydroxy-4-methyl-thieno[3,2-c]pyridine-6-carboxylic acid methyl ester

HRID 2368739
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HRID 2368739 반응식
[CH3:1][O:2][C:3]([C:5]1[N:10]=[C:9](Br)[C:8]2[C:12]([C:15]3[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=3)=[CH:13][S:14][C:7]=2[C:6]=1[OH:22])=[O:4].[CH3:23]C1(C)CCCB(C)O1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.C(OCC)(=O)C.[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>[CH3:1][O:2][C:3]([C:5]1[N:10]=[C:9]([CH3:23])[C:8]2[C:12]([C:15]3[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=3)=[CH:13][S:14][C:7]=2[C:6]=1[OH:22])=[O:4]
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참가 물질

7

반응물 3

HCID 11430Potassium CarbonateHCID 22327867TrimethylboroxaneHCID 866075134-Bromo-3-(4-fluoro-phenyl)-7-hydroxy-thieno[3,2-c]pyridine-6-carboxylic acid methyl ester

생성물 1

HCID 672338603-(4-Fluoro-phenyl)-7-hydroxy-4-methyl-thieno[3,2-c]pyridine-6-carboxylic acid methyl ester수율 56.8%

시약·촉매·용매 3

HCID 11979704
Tetrakis(triphenylphosphine)palladium
촉매
HCID 8857Ethyl Acetate용매
HCID 312751,4-Dioxane용매

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온도
100 °C

실험 절차

Under a nitrogen atmosphere, a mixture of 4-bromo-3-(4-fluoro-phenyl)-7-hydroxy-thieno[3,2-c]pyridine-6-carboxylic acid methyl ester (77.9 mg, 0.204 mmol), example 32-a, trimethylboroxane (57.0 μL, 0.408 mmol), potassium carbonate (169 mg, 1.22 mmol), and tetrakis(triphenylphosphine)-palladium(0) (35.3 mg, 0.031 mmol) were suspended in 3.5 mL of anhydrous 1,4-dioxane. The reaction mixture was heated at 100° C. for 16 hours, cooled to room temperature, and diluted with ethyl acetate. The organic mixture was successively washed with water, saturated sodium bicarbonate, and brine solutions. The organic fractions were dried over anhydrous sodium sulfate and concentrated. The crude product was purified by flash chromatography eluting from silica gel with a gradient of 0-50% ethyl acetate in hexanes to produce 36.8 mg of a white solid. MS: (+) m/z 318.0 (M+1).

후처리

  1. temperaturecooled to room temperature
  2. washThe organic mixture was successively washed with water, saturated sodium bicarbonate, and brine solutions
  3. dry with materialThe organic fractions were dried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. customThe crude product was purified by flash chromatography
  6. washeluting from silica gel with a gradient of 0-50% ethyl acetate in hexanes

출처 및 근거

ORD 기록
ord-2edde544914244a691e4cd798e739f01
출처 데이터셋
uspto-grants-2014_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08703795B2

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