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

HRID 1465952노트

반응식

HRID 1465952 반응식
[CH3:1][O:2][C:3]([CH:5]1[N:10](CC2C=CC(OC)=CC=2OC)[CH2:9][C:8]2[C:22]([C:25]3[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=3)=[CH:23][S:24][C:7]=2[C:6]1=[O:32])=[O:4].S(Cl)(Cl)=O>ClCCl>[CH3:1][O:2][C:3]([C:5]1[N:10]=[CH:9][C:8]2[C:22]([C:25]3[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=3)=[CH:23][S:24][C:7]=2[C:6]=1[OH:32])=[O:4]

참가 물질

4

반응물 2

HCID 24386Thionyl ChlorideHCID 672335175-(2,4-Dimethoxy-benzyl)3-(4-fluoro-phenyl)-7-oxo-4,5,6,7-tetrahydro-thieno[3,2-c]pyridine-6-carboxylic acid methyl ester

생성물 1

HCID 672328323-(4-Fluoro-phenyl)-7-hydroxy-thieno[3,2-c]pyridine-6-carboxylic acid methyl ester수율 61.3%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

5-(2,4-dimethoxy-benzyl)-3-(4-fluoro-phenyl)-7-oxo-4,5,6,7-tetrahydro-thieno[3,2-c]pyridine-6-carboxylic acid methyl ester (0.39 g, 0.86 mmol), example 31-e, was dissolved in 6 mL of anhydrous dichloromethane. To the solution was added 93.7 μL of thionyl chloride, and the reaction mixture was stirred for 5 hours. The solution was filtered on a fine glass frit filter to collect a white solid precipitate. The solid was washed twice with cold dichloromethane and then partitioned between saturated sodium bicarbonate solution and ethyl acetate. The organic fraction was washed with brine, dried over anhydrous sodium sulfate, and concentrated to produce 0.16 g of a white solid. MS: (+) m/z 304.0 (M+1)

후처리

  1. filtrationThe solution was filtered on a fine glass frit
  2. filtrationfilter
  3. customto collect a white solid precipitate
  4. washThe solid was washed twice with cold dichloromethane
  5. custompartitioned between saturated sodium bicarbonate solution and ethyl acetate
  6. washThe organic fraction was washed with brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated

출처 및 근거

ORD 기록
ord-f646457a525e49aba8c65efac2322d41
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09000006B2

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