4-Bromo-3-(4-fluoro-phenyl)-7-hydroxy-thieno[3,2-c]pyridine-6-carboxylic acid methyl ester → 4-Cyano-3-(4-fluoro-phenyl)-7-hydroxy-thieno[3,2-c]pyridine-6-carboxylic acid methyl ester

HRID 1465955노트

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HRID 1465955 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].[Cu][C:24]#[N:25]>CN(C=O)C>[CH3:1][O:2][C:3]([C:5]1[N:10]=[C:9]([C:24]#[N:25])[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]

참가 물질

4

반응물 2

HCID 866075134-Bromo-3-(4-fluoro-phenyl)-7-hydroxy-thieno[3,2-c]pyridine-6-carboxylic acid methyl esterHCID 178418546HCID 178418546, 화합물

생성물 1

HCID 672335184-Cyano-3-(4-fluoro-phenyl)-7-hydroxy-thieno[3,2-c]pyridine-6-carboxylic acid methyl ester수율 30.1%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
150 °C

실험 절차

A mixture of 4-bromo-3-(4-fluoro-phenyl)-7-hydroxy-thieno[3,2-c]pyridine-6-carboxylic acid methyl ester (58.5 mg, 0.153 mmol), example 32-a, and copper(I) cyanide (27.4 mg, 0.306 mmol) suspended in 1.5 mL of DMF was heated at 150° C. for 30 minutes. The resultant mixture was partitioned between ethyl acetate and water, and the organic fraction was washed with brine, dried over anhydrous sodium sulfate, and concentrated. The crude product was purified by flash chromatography eluting from silica gel with a gradient of 0-20% methanol in methylene chloride to produce 15.1 mg of a white solid. MS: (+) m/z 329.0 (M+1).

후처리

  1. customThe resultant mixture was partitioned between ethyl acetate and water
  2. washthe organic fraction was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. customThe crude product was purified by flash chromatography
  6. washeluting from silica gel with a gradient of 0-20% methanol in methylene chloride

출처 및 근거

ORD 기록
ord-daf44d84b14546b4b15970ab5a39457c
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09000006B2

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